diff --git a/.gitattributes b/.gitattributes new file mode 100644 index 0000000000000000000000000000000000000000..cc038a71cf9ff12e817f8c7c8b4871e4d613a123 --- /dev/null +++ b/.gitattributes @@ -0,0 +1,10 @@ +# Published datasets under data/ are stored in Git LFS; clones fetch the objects +# from the Hugging Face mirror (see .lfsconfig) to conserve GitHub bandwidth. +# +# LFS is scoped to data/ on purpose: a new submission staged at the repository +# root is an ordinary git file with no LFS filter, so it can be pushed from a +# fork without any LFS configuration. The submission workflow renames it into +# data/ (process_dataset --update), at which point it becomes an LFS object. +data/**/*.pb filter=lfs diff=lfs merge=lfs -text +data/**/*.pb.gz filter=lfs diff=lfs merge=lfs -text +data/**/*.parquet filter=lfs diff=lfs merge=lfs -text diff --git a/CITATION.cff b/CITATION.cff new file mode 100644 index 0000000000000000000000000000000000000000..f4ec33fc63d265cb80a99d5092a0e9d340489810 --- /dev/null +++ b/CITATION.cff @@ -0,0 +1,41 @@ +cff-version: 1.2.0 +title: The Open Reaction Database +message: If you use this dataset, please cite it using the metadata from this file. +type: dataset +authors: + - name: Open Reaction Database Project +identifiers: + - type: doi + value: 10.5281/zenodo.4321713 +url: 'https://open-reaction-database.org' +repository: 'https://github.com/open-reaction-database/ord-data' +license: CC-BY-SA-4.0 +preferred-citation: + type: article + title: The Open Reaction Database + authors: + - family-names: Kearnes + given-names: Steven M. + - family-names: Maser + given-names: Michael R. + - family-names: Wleklinski + given-names: Michael + - family-names: Kast + given-names: Anton + - family-names: Doyle + given-names: Abigail G. + - family-names: Dreher + given-names: Spencer D. + - family-names: Hawkins + given-names: Joel M. + - family-names: Jensen + given-names: Klavs F. + - family-names: Coley + given-names: Connor W. + journal: Journal of the American Chemical Society + year: 2021 + volume: 143 + issue: 45 + start: 18820 + end: 18826 + doi: 10.1021/jacs.1c09820 diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md new file mode 100644 index 0000000000000000000000000000000000000000..ca9389986dca0cc49f84b9c271e1624ddec2b782 --- /dev/null +++ b/CONTRIBUTING.md @@ -0,0 +1,113 @@ +# Contributing to the Open Reaction Database + +Thanks for helping out! What would you like to do? + +* [Report an issue](#report-an-issue) +* [Suggest an improvement (such as a new dataset)](#suggest-an-improvement) +* [Submit a new dataset](#submit-a-new-dataset) + +## Report an issue + +Sorry to hear that you're having trouble! Please [file a bug report](https://github.com/Open-Reaction-Database/ord-data/issues/new?assignees=&labels=bug&template=bug_report.md&title=) to tell us about the problem. + +## Suggest an improvement + +Great idea! Please [create a feature request](https://github.com/Open-Reaction-Database/ord-data/issues/new?assignees=&labels=enhancement&template=feature_request.md&title=) to let us know what you'd like to see. + +## Submit a new dataset + +Excellent! Please follow the +[Submission Workflow](https://ord-schema.readthedocs.io/en/latest/submissions.html) +in the documentation. + +**Note on the target branch:** open your pull request against `main`. If it adds +or changes dataset files, a workflow moves it onto a `#` branch in this +repository and comments to say so — your diff is unchanged and nothing is +required from you. That branch exists because the submission workflow pushes the +processed dataset back (assigning reaction and dataset IDs, moving files into +`data/`), which GitHub Actions cannot do on a fork. + +**Note on large files (Git LFS):** Published datasets under `data/` are stored +with [Git LFS](https://git-lfs.com/), and clones fetch the objects from the +[Hugging Face mirror](https://huggingface.co/datasets/open-reaction-database/ord-data) +to conserve GitHub bandwidth. A new submission staged at the repository root is +an ordinary file, so you can push it from a fork with no LFS setup; the +submission workflow moves it into `data/` for you. + +Only if you push changes to a file that already lives under `data/` (i.e. an LFS +object) do you need to point LFS uploads at your own fork first, since you cannot +write to the canonical repository's LFS store: + +``` +git config lfs.pushurl https://github.com//ord-data.git/info/lfs +``` + +## Terms of Use + +By submitting Contributions (as defined below) to this project, you agree that +You (as defined below) and your Contributions are bound to the following terms. + +

Open Reaction Database Project License Agreement

+ +In order to clarify the intellectual property license granted with Contributions +to the Open Access Reaction Database from any person or entity, the You must +indicate agreement to the license terms below. + +You accept and agree to the following terms and conditions for Your present and +future Contributions submitted to ORDP. Except for the license granted herein to +ORDP and recipients of data distributed by ORDP, You reserve all right, title, +and interest in and to Your Contributions. + +1. Definitions. "You" (or "Your") shall mean the copyright owner or legal entity +authorized by the copyright owner that is making this Agreement with ORDP. For +legal entities, the entity making a Contribution and all other entities that +control, are controlled by, or are under common control with that entity are +considered to be a single Contributor. For the purposes of this definition, +"control" means (i) the power, direct or indirect, to cause the direction or +management of such entity, whether by contract or otherwise, or (ii) ownership +of fifty percent (50%) or more of the outstanding shares, or (iii) beneficial +ownership of such entity. "Contribution" shall mean the data, code, +documentation or any original work of authorship, including any modifications or +additions to an existing work, that is intentionally submitted by You to ORDP +for inclusion in the Open Reaction Database managed by ORDP (the "Work"). For +the purposes of this definition, "submitted" means any form of electronic or +written communication sent to ORDP or its representatives, including but not +limited to communication on electronic mailing lists, but excluding +communication that is conspicuously marked or otherwise designated in writing by +You as "Not a Contribution." + +2. Grant of Copyright License. Subject to the terms and conditions of this +Agreement, You hereby grant to ORDP and to recipients of the data, software, or +documentation distributed by ORDP a perpetual, worldwide, non-exclusive, +no-charge, royalty-free, irrevocable copyright license to reproduce, prepare +derivative works of, publicly display, publicly perform, sublicense, and +distribute Your Contributions and such derivative works. + +3. Grant of Patent License. Subject to the terms and conditions of this +Agreement, You hereby grant to ORDP and to recipients of software distributed by +ORDP a perpetual, worldwide, non-exclusive, no-charge, royalty-free, irrevocable +(except as stated in this section) patent license to make, have made, use, offer +to sell, sell, import, and otherwise transfer the Work, where such license +applies only to those patent claims licensable by You that are necessarily +infringed by Your Contribution(s) alone or by combination of Your +Contribution(s) with the Work to which such Contribution(s) was submitted. If +any entity institutes patent litigation against You or any other entity +(including a cross-claim or counterclaim in a lawsuit) alleging that your +Contribution, or the Work to which you have contributed, constitutes direct or +contributory patent infringement, then any patent licenses granted to that +entity under this Agreement for that Contribution or Work shall terminate as of +the date such litigation is filed. + +4. You represent that you are legally entitled to grant the above license. If +your employer(s) has rights to intellectual property that you create that +includes your Contributions, you represent that you have received permission to +make Contributions on behalf of that employer, or that your employer has waived +such rights for your Contributions to ORDP. + +5. You are not expected to provide support for Your Contributions, except to the +extent You desire to provide support. You may provide support for free, for a +fee, or not at all. Unless required by applicable law or agreed to in writing, +You provide Your Contributions on an "AS IS" BASIS, WITHOUT WARRANTIES OR +CONDITIONS OF ANY KIND, either express or implied, including, without +limitation, any warranties or conditions of TITLE, NON-INFRINGEMENT, +MERCHANTABILITY, or FITNESS FOR A PARTICULAR PURPOSE. diff --git a/CONTRIBUTORS.md b/CONTRIBUTORS.md new file mode 100644 index 0000000000000000000000000000000000000000..fe1e8b467689946a00fc7714840eee39eb44ae6c --- /dev/null +++ b/CONTRIBUTORS.md @@ -0,0 +1,15 @@ +# Contributors to the Open Reaction Database + +This list includes both submitters and reviewers. +Without your contributions, the Open Reaction Database could not exist! + +| Name | GitHub Username | Institution | +| ---- | --------------- | ----------- | +| Connor Coley | [@connorcoley](https://github.com/connorcoley) | MIT | +| Steven Kearnes | [@skearnes](https://github.com/skearnes) | Relay | +| Jun Li | [@jun-li-2020](https://github.com/jun-li-2020) | BMS | +| Fabio Lima | [@limafabio2](https://github.com/limafabio2) | Novartis | +| Jesus Martinez Alvarado | [@Jesus00-1](https://github.com/Jesus00-1) | Princeton | +| Michael Maser | [@michaelmaser](https://github.com/michaelmaser) | Caltech | +| Jason Wang | [@beef-broccoli](https://github.com/beef-broccoli) | Princeton | +| Michael Wleklinski | [@mwleklin](https://github.com/mwleklin) | Merck | diff --git a/LICENSE b/LICENSE new file mode 100644 index 0000000000000000000000000000000000000000..cc3e2459dc5c46f1936b6e3b54137099063818e0 --- /dev/null +++ b/LICENSE @@ -0,0 +1,427 @@ +Attribution-ShareAlike 4.0 International + +======================================================================= + +Creative Commons Corporation ("Creative Commons") is not a law firm and +does not provide legal services or legal advice. Distribution of +Creative Commons public licenses does not create a lawyer-client or +other relationship. Creative Commons makes its licenses and related +information available on an "as-is" basis. Creative Commons gives no +warranties regarding its licenses, any material licensed under their +terms and conditions, or any related information. Creative Commons +disclaims all liability for damages resulting from their use to the +fullest extent possible. + +Using Creative Commons Public Licenses + +Creative Commons public licenses provide a standard set of terms and +conditions that creators and other rights holders may use to share +original works of authorship and other material subject to copyright +and certain other rights specified in the public license below. The +following considerations are for informational purposes only, are not +exhaustive, and do not form part of our licenses. + + Considerations for licensors: Our public licenses are + intended for use by those authorized to give the public + permission to use material in ways otherwise restricted by + copyright and certain other rights. Our licenses are + irrevocable. Licensors should read and understand the terms + and conditions of the license they choose before applying it. + Licensors should also secure all rights necessary before + applying our licenses so that the public can reuse the + material as expected. Licensors should clearly mark any + material not subject to the license. This includes other CC- + licensed material, or material used under an exception or + limitation to copyright. More considerations for licensors: + wiki.creativecommons.org/Considerations_for_licensors + + Considerations for the public: By using one of our public + licenses, a licensor grants the public permission to use the + licensed material under specified terms and conditions. If + the licensor's permission is not necessary for any reason--for + example, because of any applicable exception or limitation to + copyright--then that use is not regulated by the license. Our + licenses grant only permissions under copyright and certain + other rights that a licensor has authority to grant. Use of + the licensed material may still be restricted for other + reasons, including because others have copyright or other + rights in the material. A licensor may make special requests, + such as asking that all changes be marked or described. + Although not required by our licenses, you are encouraged to + respect those requests where reasonable. More considerations + for the public: + wiki.creativecommons.org/Considerations_for_licensees + +======================================================================= + +Creative Commons Attribution-ShareAlike 4.0 International Public +License + +By exercising the Licensed Rights (defined below), You accept and agree +to be bound by the terms and conditions of this Creative Commons +Attribution-ShareAlike 4.0 International Public License ("Public +License"). To the extent this Public License may be interpreted as a +contract, You are granted the Licensed Rights in consideration of Your +acceptance of these terms and conditions, and the Licensor grants You +such rights in consideration of benefits the Licensor receives from +making the Licensed Material available under these terms and +conditions. + + +Section 1 -- Definitions. + + a. Adapted Material means material subject to Copyright and Similar + Rights that is derived from or based upon the Licensed Material + and in which the Licensed Material is translated, altered, + arranged, transformed, or otherwise modified in a manner requiring + permission under the Copyright and Similar Rights held by the + Licensor. For purposes of this Public License, where the Licensed + Material is a musical work, performance, or sound recording, + Adapted Material is always produced where the Licensed Material is + synched in timed relation with a moving image. + + b. Adapter's License means the license You apply to Your Copyright + and Similar Rights in Your contributions to Adapted Material in + accordance with the terms and conditions of this Public License. + + c. BY-SA Compatible License means a license listed at + creativecommons.org/compatiblelicenses, approved by Creative + Commons as essentially the equivalent of this Public License. + + d. Copyright and Similar Rights means copyright and/or similar rights + closely related to copyright including, without limitation, + performance, broadcast, sound recording, and Sui Generis Database + Rights, without regard to how the rights are labeled or + categorized. For purposes of this Public License, the rights + specified in Section 2(b)(1)-(2) are not Copyright and Similar + Rights. + + e. Effective Technological Measures means those measures that, in the + absence of proper authority, may not be circumvented under laws + fulfilling obligations under Article 11 of the WIPO Copyright + Treaty adopted on December 20, 1996, and/or similar international + agreements. + + f. Exceptions and Limitations means fair use, fair dealing, and/or + any other exception or limitation to Copyright and Similar Rights + that applies to Your use of the Licensed Material. + + g. License Elements means the license attributes listed in the name + of a Creative Commons Public License. The License Elements of this + Public License are Attribution and ShareAlike. + + h. Licensed Material means the artistic or literary work, database, + or other material to which the Licensor applied this Public + License. + + i. Licensed Rights means the rights granted to You subject to the + terms and conditions of this Public License, which are limited to + all Copyright and Similar Rights that apply to Your use of the + Licensed Material and that the Licensor has authority to license. + + j. Licensor means the individual(s) or entity(ies) granting rights + under this Public License. + + k. Share means to provide material to the public by any means or + process that requires permission under the Licensed Rights, such + as reproduction, public display, public performance, distribution, + dissemination, communication, or importation, and to make material + available to the public including in ways that members of the + public may access the material from a place and at a time + individually chosen by them. + + l. Sui Generis Database Rights means rights other than copyright + resulting from Directive 96/9/EC of the European Parliament and of + the Council of 11 March 1996 on the legal protection of databases, + as amended and/or succeeded, as well as other essentially + equivalent rights anywhere in the world. + + m. You means the individual or entity exercising the Licensed Rights + under this Public License. Your has a corresponding meaning. + + +Section 2 -- Scope. + + a. License grant. + + 1. Subject to the terms and conditions of this Public License, + the Licensor hereby grants You a worldwide, royalty-free, + non-sublicensable, non-exclusive, irrevocable license to + exercise the Licensed Rights in the Licensed Material to: + + a. reproduce and Share the Licensed Material, in whole or + in part; and + + b. produce, reproduce, and Share Adapted Material. + + 2. Exceptions and Limitations. For the avoidance of doubt, where + Exceptions and Limitations apply to Your use, this Public + License does not apply, and You do not need to comply with + its terms and conditions. + + 3. Term. The term of this Public License is specified in Section + 6(a). + + 4. Media and formats; technical modifications allowed. The + Licensor authorizes You to exercise the Licensed Rights in + all media and formats whether now known or hereafter created, + and to make technical modifications necessary to do so. The + Licensor waives and/or agrees not to assert any right or + authority to forbid You from making technical modifications + necessary to exercise the Licensed Rights, including + technical modifications necessary to circumvent Effective + Technological Measures. For purposes of this Public License, + simply making modifications authorized by this Section 2(a) + (4) never produces Adapted Material. + + 5. Downstream recipients. + + a. Offer from the Licensor -- Licensed Material. Every + recipient of the Licensed Material automatically + receives an offer from the Licensor to exercise the + Licensed Rights under the terms and conditions of this + Public License. + + b. Additional offer from the Licensor -- Adapted Material. + Every recipient of Adapted Material from You + automatically receives an offer from the Licensor to + exercise the Licensed Rights in the Adapted Material + under the conditions of the Adapter's License You apply. + + c. No downstream restrictions. You may not offer or impose + any additional or different terms or conditions on, or + apply any Effective Technological Measures to, the + Licensed Material if doing so restricts exercise of the + Licensed Rights by any recipient of the Licensed + Material. + + 6. No endorsement. Nothing in this Public License constitutes or + may be construed as permission to assert or imply that You + are, or that Your use of the Licensed Material is, connected + with, or sponsored, endorsed, or granted official status by, + the Licensor or others designated to receive attribution as + provided in Section 3(a)(1)(A)(i). + + b. Other rights. + + 1. Moral rights, such as the right of integrity, are not + licensed under this Public License, nor are publicity, + privacy, and/or other similar personality rights; however, to + the extent possible, the Licensor waives and/or agrees not to + assert any such rights held by the Licensor to the limited + extent necessary to allow You to exercise the Licensed + Rights, but not otherwise. + + 2. Patent and trademark rights are not licensed under this + Public License. + + 3. To the extent possible, the Licensor waives any right to + collect royalties from You for the exercise of the Licensed + Rights, whether directly or through a collecting society + under any voluntary or waivable statutory or compulsory + licensing scheme. In all other cases the Licensor expressly + reserves any right to collect such royalties. + + +Section 3 -- License Conditions. + +Your exercise of the Licensed Rights is expressly made subject to the +following conditions. + + a. Attribution. + + 1. If You Share the Licensed Material (including in modified + form), You must: + + a. retain the following if it is supplied by the Licensor + with the Licensed Material: + + i. identification of the creator(s) of the Licensed + Material and any others designated to receive + attribution, in any reasonable manner requested by + the Licensor (including by pseudonym if + designated); + + ii. a copyright notice; + + iii. a notice that refers to this Public License; + + iv. a notice that refers to the disclaimer of + warranties; + + v. a URI or hyperlink to the Licensed Material to the + extent reasonably practicable; + + b. indicate if You modified the Licensed Material and + retain an indication of any previous modifications; and + + c. indicate the Licensed Material is licensed under this + Public License, and include the text of, or the URI or + hyperlink to, this Public License. + + 2. You may satisfy the conditions in Section 3(a)(1) in any + reasonable manner based on the medium, means, and context in + which You Share the Licensed Material. For example, it may be + reasonable to satisfy the conditions by providing a URI or + hyperlink to a resource that includes the required + information. + + 3. If requested by the Licensor, You must remove any of the + information required by Section 3(a)(1)(A) to the extent + reasonably practicable. + + b. ShareAlike. + + In addition to the conditions in Section 3(a), if You Share + Adapted Material You produce, the following conditions also apply. + + 1. The Adapter's License You apply must be a Creative Commons + license with the same License Elements, this version or + later, or a BY-SA Compatible License. + + 2. You must include the text of, or the URI or hyperlink to, the + Adapter's License You apply. You may satisfy this condition + in any reasonable manner based on the medium, means, and + context in which You Share Adapted Material. + + 3. You may not offer or impose any additional or different terms + or conditions on, or apply any Effective Technological + Measures to, Adapted Material that restrict exercise of the + rights granted under the Adapter's License You apply. + + +Section 4 -- Sui Generis Database Rights. + +Where the Licensed Rights include Sui Generis Database Rights that +apply to Your use of the Licensed Material: + + a. for the avoidance of doubt, Section 2(a)(1) grants You the right + to extract, reuse, reproduce, and Share all or a substantial + portion of the contents of the database; + + b. if You include all or a substantial portion of the database + contents in a database in which You have Sui Generis Database + Rights, then the database in which You have Sui Generis Database + Rights (but not its individual contents) is Adapted Material, + + including for purposes of Section 3(b); and + c. You must comply with the conditions in Section 3(a) if You Share + all or a substantial portion of the contents of the database. + +For the avoidance of doubt, this Section 4 supplements and does not +replace Your obligations under this Public License where the Licensed +Rights include other Copyright and Similar Rights. + + +Section 5 -- Disclaimer of Warranties and Limitation of Liability. + + a. UNLESS OTHERWISE SEPARATELY UNDERTAKEN BY THE LICENSOR, TO THE + EXTENT POSSIBLE, THE LICENSOR OFFERS THE LICENSED MATERIAL AS-IS + AND AS-AVAILABLE, AND MAKES NO REPRESENTATIONS OR WARRANTIES OF + ANY KIND CONCERNING THE LICENSED MATERIAL, WHETHER EXPRESS, + IMPLIED, STATUTORY, OR OTHER. THIS INCLUDES, WITHOUT LIMITATION, + WARRANTIES OF TITLE, MERCHANTABILITY, FITNESS FOR A PARTICULAR + PURPOSE, NON-INFRINGEMENT, ABSENCE OF LATENT OR OTHER DEFECTS, + ACCURACY, OR THE PRESENCE OR ABSENCE OF ERRORS, WHETHER OR NOT + KNOWN OR DISCOVERABLE. WHERE DISCLAIMERS OF WARRANTIES ARE NOT + ALLOWED IN FULL OR IN PART, THIS DISCLAIMER MAY NOT APPLY TO YOU. + + b. TO THE EXTENT POSSIBLE, IN NO EVENT WILL THE LICENSOR BE LIABLE + TO YOU ON ANY LEGAL THEORY (INCLUDING, WITHOUT LIMITATION, + NEGLIGENCE) OR OTHERWISE FOR ANY DIRECT, SPECIAL, INDIRECT, + INCIDENTAL, CONSEQUENTIAL, PUNITIVE, EXEMPLARY, OR OTHER LOSSES, + COSTS, EXPENSES, OR DAMAGES ARISING OUT OF THIS PUBLIC LICENSE OR + USE OF THE LICENSED MATERIAL, EVEN IF THE LICENSOR HAS BEEN + ADVISED OF THE POSSIBILITY OF SUCH LOSSES, COSTS, EXPENSES, OR + DAMAGES. WHERE A LIMITATION OF LIABILITY IS NOT ALLOWED IN FULL OR + IN PART, THIS LIMITATION MAY NOT APPLY TO YOU. + + c. The disclaimer of warranties and limitation of liability provided + above shall be interpreted in a manner that, to the extent + possible, most closely approximates an absolute disclaimer and + waiver of all liability. + + +Section 6 -- Term and Termination. + + a. This Public License applies for the term of the Copyright and + Similar Rights licensed here. However, if You fail to comply with + this Public License, then Your rights under this Public License + terminate automatically. + + b. Where Your right to use the Licensed Material has terminated under + Section 6(a), it reinstates: + + 1. automatically as of the date the violation is cured, provided + it is cured within 30 days of Your discovery of the + violation; or + + 2. upon express reinstatement by the Licensor. + + For the avoidance of doubt, this Section 6(b) does not affect any + right the Licensor may have to seek remedies for Your violations + of this Public License. + + c. For the avoidance of doubt, the Licensor may also offer the + Licensed Material under separate terms or conditions or stop + distributing the Licensed Material at any time; however, doing so + will not terminate this Public License. + + d. Sections 1, 5, 6, 7, and 8 survive termination of this Public + License. + + +Section 7 -- Other Terms and Conditions. + + a. The Licensor shall not be bound by any additional or different + terms or conditions communicated by You unless expressly agreed. + + b. Any arrangements, understandings, or agreements regarding the + Licensed Material not stated herein are separate from and + independent of the terms and conditions of this Public License. + + +Section 8 -- Interpretation. + + a. For the avoidance of doubt, this Public License does not, and + shall not be interpreted to, reduce, limit, restrict, or impose + conditions on any use of the Licensed Material that could lawfully + be made without permission under this Public License. + + b. To the extent possible, if any provision of this Public License is + deemed unenforceable, it shall be automatically reformed to the + minimum extent necessary to make it enforceable. If the provision + cannot be reformed, it shall be severed from this Public License + without affecting the enforceability of the remaining terms and + conditions. + + c. No term or condition of this Public License will be waived and no + failure to comply consented to unless expressly agreed to by the + Licensor. + + d. Nothing in this Public License constitutes or may be interpreted + as a limitation upon, or waiver of, any privileges and immunities + that apply to the Licensor or You, including from the legal + processes of any jurisdiction or authority. + + +======================================================================= + +Creative Commons is not a party to its public +licenses. Notwithstanding, Creative Commons may elect to apply one of +its public licenses to material it publishes and in those instances +will be considered the “Licensor.” The text of the Creative Commons +public licenses is dedicated to the public domain under the CC0 Public +Domain Dedication. Except for the limited purpose of indicating that +material is shared under a Creative Commons public license or as +otherwise permitted by the Creative Commons policies published at +creativecommons.org/policies, Creative Commons does not authorize the +use of the trademark "Creative Commons" or any other trademark or logo +of Creative Commons without its prior written consent including, +without limitation, in connection with any unauthorized modifications +to any of its public licenses or any other arrangements, +understandings, or agreements concerning use of licensed material. For +the avoidance of doubt, this paragraph does not form part of the +public licenses. + +Creative Commons may be contacted at creativecommons.org. diff --git a/README.md b/README.md new file mode 100644 index 0000000000000000000000000000000000000000..56fa35bf4c33847c146589392be3f2cf945cc431 --- /dev/null +++ b/README.md @@ -0,0 +1,540 @@ +--- +license: cc-by-sa-4.0 +tags: +- chemistry +- reactions +- cheminformatics +pretty_name: The Open Reaction Database +configs: +- config_name: default + default: true + data_files: + - data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.parquet + - data/03/ord_dataset-0316886541d9435489859c2ad7edc863.parquet + - data/0c/ord_dataset-0c75d67751634f0594b24b9f498b77c2.parquet + - data/10/ord_dataset-10b940e7982c4622b1e1ac879394aba6.parquet + - data/17/ord_dataset-172039a759a440219a68af62d203b79b.parquet + - data/1d/ord_dataset-1d3a1a6fb70d46c084602d0688967afc.parquet + - data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.parquet + - data/20/ord_dataset-2038a3c967db4a32a8fbce288437e929.parquet + - data/2b/ord_dataset-2be11f57f3304e678ea8469baf6dd1bc.parquet + - data/2b/ord_dataset-2be30f5d8dcd471aa6ad410bdee05902.parquet + - data/31/ord_dataset-31989f1b2b9d4885b1dd2d9982da4517.parquet + - data/35/ord_dataset-35a5a513f1dd44a3a97c88da99f81a00.parquet + - data/3b/ord_dataset-3b5db90e337942ea886b8f5bc5e3aa72.parquet + - data/3b/ord_dataset-3b8a2ef300e145468579027f206a3ac8.parquet + - data/46/ord_dataset-46ff9a32d9e04016b9380b1b1ef949c3.parquet + - data/47/ord_dataset-47eaacc46c3a4487bbdf99adb1a15e41.parquet + - data/4d/ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6.parquet + - data/52/ord_dataset-52bd3b0ec72c443aab113bcea09bf3f4.parquet + - data/54/ord_dataset-5415f83da68e4797856ddd330dda5c61.parquet + - data/55/ord_dataset-5540e162c09f4c04905ddc8ba9c931c6.parquet + - data/55/ord_dataset-55de08a995554f558c25fc43eac62359.parquet + - data/5c/ord_dataset-5c9a10329a8a48968d18879a48bb8ab2.parquet + - data/5e/ord_dataset-5e8318f0dda04b398c14f4c3adfeb32c.parquet + - data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet + - data/67/ord_dataset-675eddcaa6674ce3ae61e79bbc1e1c08.parquet + - data/68/ord_dataset-68cb8b4b2b384e3d85b5b1efae58b203.parquet + - data/6a/ord_dataset-6a0bfcdf53a64c07987822162ae591e2.parquet + - data/7a/ord_dataset-7acd6ad2bf4d4cff841cad008ab726d5.parquet + - data/7d/ord_dataset-7d8f5fd922d4497d91cb81489b052746.parquet + - data/80/ord_dataset-805ad863feef48579d95d86a728035f4.parquet + - data/89/ord_dataset-89b083710e2d441aa0040c361d63359f.parquet + - data/8d/ord_dataset-8d1e28ec1f6b4ee8ad372e0b5ed7a62e.parquet + - data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet + - data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet + - data/a1/ord_dataset-a12fa15d036d489c971b0b514caeae52.parquet + - data/ac/ord_dataset-ac78456835404910b3a4c840248b6ac9.parquet + - data/b4/ord_dataset-b440f8c90b6343189093770060fc4098.parquet + - data/bc/ord_dataset-bc349c19b4384756a2aee8aa525b6c2a.parquet + - data/c5/ord_dataset-c5b00523487a4211a194160edf45e9ab.parquet + - data/c7/ord_dataset-c703268ea43a4c7e802c6048b6166b34.parquet + - data/cb/ord_dataset-cbcc4048add7468e850b6ec42549c70d.parquet + - data/ce/ord_dataset-ce5045aceb214cfc8bfd0ef3031e2737.parquet + - data/d2/ord_dataset-d26118acda314269becc35db5c22dc59.parquet + - data/d3/ord_dataset-d319c2a22ecf4ce59db1a18ae71d529c.parquet + - data/d9/ord_dataset-d92976309c3a48a3a64a4cf5e7048086.parquet + - data/dc/ord_dataset-dc0249930af34d17a3c76881a762aebf.parquet + - data/ee/ord_dataset-eeba974d3c284aed86d1c1d442260a1e.parquet + - data/fc/ord_dataset-fc83743b978f4deea7d6856deacbfe53.parquet + - data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet +- config_name: uspto-grants + data_files: + - data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +- config_name: uspto-mit + data_files: + - split: train + path: data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet + - split: validation + path: data/54/ord_dataset-5481550056a14935b76e031fb94b88be.parquet + - split: test + path: data/48/ord_dataset-488402f6ec0d441ca2f7d6fabea7c220.parquet +- config_name: ord_dataset-00005539a1e04c809a9a78647bea649c + data_files: + - data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.parquet +- config_name: ord_dataset-0316886541d9435489859c2ad7edc863 + data_files: + - data/03/ord_dataset-0316886541d9435489859c2ad7edc863.parquet +- config_name: ord_dataset-0c75d67751634f0594b24b9f498b77c2 + data_files: + - data/0c/ord_dataset-0c75d67751634f0594b24b9f498b77c2.parquet +- config_name: ord_dataset-10b940e7982c4622b1e1ac879394aba6 + data_files: + - data/10/ord_dataset-10b940e7982c4622b1e1ac879394aba6.parquet +- config_name: ord_dataset-1158e351757f315b93cbcbe7bc55f38e + data_files: + - data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +- config_name: ord_dataset-172039a759a440219a68af62d203b79b + data_files: + - data/17/ord_dataset-172039a759a440219a68af62d203b79b.parquet +- config_name: ord_dataset-1d3a1a6fb70d46c084602d0688967afc + data_files: + - data/1d/ord_dataset-1d3a1a6fb70d46c084602d0688967afc.parquet +- config_name: ord_dataset-1ec2807f02fa4beda27d2a81b86eb843 + data_files: + - data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.parquet +- config_name: ord_dataset-2038a3c967db4a32a8fbce288437e929 + data_files: + - data/20/ord_dataset-2038a3c967db4a32a8fbce288437e929.parquet +- config_name: ord_dataset-2be11f57f3304e678ea8469baf6dd1bc + data_files: + - data/2b/ord_dataset-2be11f57f3304e678ea8469baf6dd1bc.parquet +- config_name: ord_dataset-2be30f5d8dcd471aa6ad410bdee05902 + data_files: + - data/2b/ord_dataset-2be30f5d8dcd471aa6ad410bdee05902.parquet +- config_name: ord_dataset-31989f1b2b9d4885b1dd2d9982da4517 + data_files: + - data/31/ord_dataset-31989f1b2b9d4885b1dd2d9982da4517.parquet +- config_name: ord_dataset-35a5a513f1dd44a3a97c88da99f81a00 + data_files: + - data/35/ord_dataset-35a5a513f1dd44a3a97c88da99f81a00.parquet +- config_name: ord_dataset-3b5db90e337942ea886b8f5bc5e3aa72 + data_files: + - data/3b/ord_dataset-3b5db90e337942ea886b8f5bc5e3aa72.parquet +- config_name: ord_dataset-3b8a2ef300e145468579027f206a3ac8 + data_files: + - data/3b/ord_dataset-3b8a2ef300e145468579027f206a3ac8.parquet +- config_name: ord_dataset-46ff9a32d9e04016b9380b1b1ef949c3 + data_files: + - data/46/ord_dataset-46ff9a32d9e04016b9380b1b1ef949c3.parquet +- config_name: ord_dataset-47eaacc46c3a4487bbdf99adb1a15e41 + data_files: + - data/47/ord_dataset-47eaacc46c3a4487bbdf99adb1a15e41.parquet +- config_name: ord_dataset-488402f6ec0d441ca2f7d6fabea7c220 + data_files: + - data/48/ord_dataset-488402f6ec0d441ca2f7d6fabea7c220.parquet +- config_name: ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6 + data_files: + - data/4d/ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6.parquet +- config_name: ord_dataset-52bd3b0ec72c443aab113bcea09bf3f4 + data_files: + - data/52/ord_dataset-52bd3b0ec72c443aab113bcea09bf3f4.parquet +- config_name: ord_dataset-5415f83da68e4797856ddd330dda5c61 + data_files: + - data/54/ord_dataset-5415f83da68e4797856ddd330dda5c61.parquet +- config_name: ord_dataset-5481550056a14935b76e031fb94b88be + data_files: + - data/54/ord_dataset-5481550056a14935b76e031fb94b88be.parquet +- config_name: ord_dataset-5540e162c09f4c04905ddc8ba9c931c6 + data_files: + - data/55/ord_dataset-5540e162c09f4c04905ddc8ba9c931c6.parquet +- config_name: ord_dataset-55de08a995554f558c25fc43eac62359 + data_files: + - data/55/ord_dataset-55de08a995554f558c25fc43eac62359.parquet +- config_name: ord_dataset-5c9a10329a8a48968d18879a48bb8ab2 + data_files: + - data/5c/ord_dataset-5c9a10329a8a48968d18879a48bb8ab2.parquet +- config_name: ord_dataset-5e8318f0dda04b398c14f4c3adfeb32c + data_files: + - data/5e/ord_dataset-5e8318f0dda04b398c14f4c3adfeb32c.parquet +- config_name: ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd + data_files: + - data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet +- config_name: ord_dataset-675eddcaa6674ce3ae61e79bbc1e1c08 + data_files: + - data/67/ord_dataset-675eddcaa6674ce3ae61e79bbc1e1c08.parquet +- config_name: ord_dataset-68cb8b4b2b384e3d85b5b1efae58b203 + data_files: + - data/68/ord_dataset-68cb8b4b2b384e3d85b5b1efae58b203.parquet +- config_name: ord_dataset-6a0bfcdf53a64c07987822162ae591e2 + data_files: + - data/6a/ord_dataset-6a0bfcdf53a64c07987822162ae591e2.parquet +- config_name: ord_dataset-7acd6ad2bf4d4cff841cad008ab726d5 + data_files: + - data/7a/ord_dataset-7acd6ad2bf4d4cff841cad008ab726d5.parquet +- config_name: ord_dataset-7d8f5fd922d4497d91cb81489b052746 + data_files: + - data/7d/ord_dataset-7d8f5fd922d4497d91cb81489b052746.parquet +- config_name: ord_dataset-805ad863feef48579d95d86a728035f4 + data_files: + - data/80/ord_dataset-805ad863feef48579d95d86a728035f4.parquet +- config_name: ord_dataset-89b083710e2d441aa0040c361d63359f + data_files: + - data/89/ord_dataset-89b083710e2d441aa0040c361d63359f.parquet +- config_name: ord_dataset-8d1e28ec1f6b4ee8ad372e0b5ed7a62e + data_files: + - data/8d/ord_dataset-8d1e28ec1f6b4ee8ad372e0b5ed7a62e.parquet +- config_name: ord_dataset-99c23cf435dc42f1af884053bc8b11c7 + data_files: + - data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet +- config_name: ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545 + data_files: + - data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet +- config_name: ord_dataset-a12fa15d036d489c971b0b514caeae52 + data_files: + - data/a1/ord_dataset-a12fa15d036d489c971b0b514caeae52.parquet +- config_name: ord_dataset-ac78456835404910b3a4c840248b6ac9 + data_files: + - data/ac/ord_dataset-ac78456835404910b3a4c840248b6ac9.parquet +- config_name: ord_dataset-b440f8c90b6343189093770060fc4098 + data_files: + - data/b4/ord_dataset-b440f8c90b6343189093770060fc4098.parquet +- config_name: ord_dataset-bc349c19b4384756a2aee8aa525b6c2a + data_files: + - data/bc/ord_dataset-bc349c19b4384756a2aee8aa525b6c2a.parquet +- config_name: ord_dataset-c5b00523487a4211a194160edf45e9ab + data_files: + - data/c5/ord_dataset-c5b00523487a4211a194160edf45e9ab.parquet +- config_name: ord_dataset-c703268ea43a4c7e802c6048b6166b34 + data_files: + - data/c7/ord_dataset-c703268ea43a4c7e802c6048b6166b34.parquet +- config_name: ord_dataset-cbcc4048add7468e850b6ec42549c70d + data_files: + - data/cb/ord_dataset-cbcc4048add7468e850b6ec42549c70d.parquet +- config_name: ord_dataset-ce5045aceb214cfc8bfd0ef3031e2737 + data_files: + - data/ce/ord_dataset-ce5045aceb214cfc8bfd0ef3031e2737.parquet +- config_name: ord_dataset-d26118acda314269becc35db5c22dc59 + data_files: + - data/d2/ord_dataset-d26118acda314269becc35db5c22dc59.parquet +- config_name: ord_dataset-d319c2a22ecf4ce59db1a18ae71d529c + data_files: + - data/d3/ord_dataset-d319c2a22ecf4ce59db1a18ae71d529c.parquet +- config_name: ord_dataset-d92976309c3a48a3a64a4cf5e7048086 + data_files: + - data/d9/ord_dataset-d92976309c3a48a3a64a4cf5e7048086.parquet +- config_name: ord_dataset-dc0249930af34d17a3c76881a762aebf + data_files: + - data/dc/ord_dataset-dc0249930af34d17a3c76881a762aebf.parquet +- config_name: ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3 + data_files: + - data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +- config_name: ord_dataset-eeba974d3c284aed86d1c1d442260a1e + data_files: + - data/ee/ord_dataset-eeba974d3c284aed86d1c1d442260a1e.parquet +- config_name: ord_dataset-fc83743b978f4deea7d6856deacbfe53 + data_files: + - data/fc/ord_dataset-fc83743b978f4deea7d6856deacbfe53.parquet +- config_name: ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc + data_files: + - data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet +--- + +# ord-data + +![](https://github.com/Open-Reaction-Database/ord-data/workflows/Validation/badge.svg) +[![DOI](https://zenodo.org/badge/283813042.svg)](https://zenodo.org/badge/latestdoi/283813042) + +## Getting the Data + +The datasets live under [`data/`](data) and are stored with +[Git LFS](https://git-lfs.com/). LFS reads are redirected to the +[Hugging Face mirror](https://huggingface.co/datasets/open-reaction-database/ord-data) +via [`.lfsconfig`](.lfsconfig), so dataset objects are fetched from Hugging +Face's CDN rather than from GitHub's shared (and limited) LFS bandwidth. This is +automatic — you do not need to configure anything. + +### Option 1: Clone the repository + +```bash +git clone https://github.com/open-reaction-database/ord-data.git +``` + +With [Git LFS](https://git-lfs.com/) installed, this pulls every dataset object +from the Hugging Face mirror and gives you the full Git history with the data in +place. + +### Option 2: Download only the data (a subset, or without Git history) + +```bash +pip install huggingface_hub +python scripts/download_from_huggingface.py +``` + +(If you use [uv](https://docs.astral.sh/uv/), `uv run scripts/download_from_huggingface.py` +installs the dependencies for you.) + +The script mirrors the `data/` directory from the Hugging Face dataset into your +local checkout. Pass `--allow-pattern 'data/4d/*.parquet'` (repeatable) to download +only a subset, or `--output-dir ` to write somewhere other than the +repository root. To skip LFS entirely during the clone and fetch the data +afterward: + +```bash +GIT_LFS_SKIP_SMUDGE=1 git clone https://github.com/open-reaction-database/ord-data.git +cd ord-data +python scripts/download_from_huggingface.py +``` + +You can also browse and download datasets directly from the +[Hugging Face dataset page](https://huggingface.co/datasets/open-reaction-database/ord-data). + +For how this LFS / Hugging Face mirror setup works (and what it means for +contributors), see +[Git LFS and the Hugging Face mirror](#git-lfs-and-the-hugging-face-mirror) +below. + +## Data Manipulation + +The `ord-data` repository contains the Open Reaction Database (ORD) as Parquet files stored in the +[`data`](data) directory. Each file holds one dataset: the reactions are serialized Protobuf +messages (one per row) and the dataset name/description/ID travel in the file metadata, so those +scalars and every reaction survive a round trip through `ord_schema`. (`Dataset.reaction_ids`, +which names reactions stored outside the dataset, is not persisted — the `reaction_id` column is +the source of truth — and a dataset with no reactions cannot be written at all.) The user can +convert the data into human readable text format, *.pbtxt. + +```python +# import requirements +from ord_schema.datasets import load_dataset +from ord_schema.message_helpers import save_message + +# load the parquet file as a Dataset proto +# (as_dataset materializes it; the default is a streaming DatasetView) +dataset = load_dataset("input_fname.parquet", as_dataset=True) +# save the ord file as human readable text +save_message(dataset, "output_fname.pbtxt") +``` + +`datasets.load_dataset` returns a `DatasetView` for Parquet, which takes the +dataset's scalars and row count from the file footer and reads reactions on +demand. (Note the name collision: `ord_schema.parquet.load_dataset` always +materializes, which on the largest file is a silent 1.8M-reaction load rather +than an error.) Iteration, `len`, indexing, and slicing over `reactions` behave +like a list, so read-only code needs no change — and the USPTO grants file, +1.8M reactions in 1.1 GB, opens in milliseconds rather than deserializing up +front. Two places the resemblance stops: indexing returns a freshly +deserialized copy rather than a live sub-message, so mutating it changes +nothing on disk, and `reactions` never compares equal to a list — compare +against `list(view.reactions)`. Pass `as_dataset=True` (above) when you need the +protobuf surface: serializing or mutating the dataset as a whole. If you already +hold a view, `to_proto()` does the same thing. + +Beyond plain iteration, a view can look a reaction up by ID with `get_reaction`, +yield IDs alone with `iter_reaction_ids`, and read one row group at a time with +`iter_reactions(row_group=...)`, which yields `(reaction_id, Reaction)` pairs +rather than bare reactions. Row groups are the unit of parallelism for fanning +out over a large file; `view.num_row_groups` gives the upper bound, and an index +outside it raises `IndexError`. + +We can also convert ORD data into JSON format. + +```python +# import requirements +import json + +from ord_schema.datasets import load_dataset +from google.protobuf.json_format import MessageToJson + +input_fname = "sample_file.parquet" +dataset = load_dataset(input_fname) + +# take one reaction message from the dataset for example +rxn = dataset.reactions[0] +rxn_json = json.loads( + MessageToJson( + message=rxn, + always_print_fields_with_no_presence=False, + preserving_proto_field_name=True, + indent=2, + sort_keys=False, + use_integers_for_enums=False, + descriptor_pool=None, + float_precision=None, + ensure_ascii=True, + ) +) + +print( + f"We have converted the {input_fname} to JSON format shown as below, \n{rxn_json}" +) +``` + +## Retired dataset IDs + +Two datasets are consolidations of shards that were once published separately, and a consolidated +output carries a new ID derived from the sorted IDs of its sources: + +| Dataset | ID | Sources | +| --- | --- | --- | +| `uspto-grants` | `ord_dataset-1158e351757f315b93cbcbe7bc55f38e` | 489 monthly `uspto-grants-YYYY_MM` datasets | +| `Training data from https://doi.org/10.1039/C8SC04228D` | `ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3` | 10 `(N/10)` shards | + +[`retired_datasets.csv`](retired_datasets.csv) maps each of the 499 retired IDs to the dataset that +replaced it. Every other dataset kept its ID. + +Per-reaction patent provenance for the USPTO data is on `Reaction.provenance.patent`, so the +monthly bucket a reaction came from is recoverable from the consolidated dataset. + +## Git LFS and the Hugging Face mirror + +Dataset files under [`data/`](data) are stored with Git LFS. Clone and fork +traffic was dominating GitHub's shared LFS bandwidth quota, so the repository is +configured to keep that traffic off GitHub while leaving GitHub authoritative +for the data: + +- **Reads come from Hugging Face.** [`.lfsconfig`](.lfsconfig) points `lfs.url` + at the + [Hugging Face mirror](https://huggingface.co/datasets/open-reaction-database/ord-data), + so clones and forks fetch LFS objects from HF's CDN instead of GitHub. +- **GitHub remains the source of truth.** LFS objects are always written to + GitHub (storage there is fine; only download bandwidth was the problem), and + the [mirror workflow](.github/workflows/huggingface_mirror.yml) copies them to + Hugging Face after every merge to `main`. Hugging Face is purely a read + replica — every object is always retrievable from GitHub. +- **LFS is scoped to `data/`** (see [`.gitattributes`](.gitattributes)). A new + dataset staged at the repository root is an ordinary Git file, so submissions + can be pushed from a fork with no LFS configuration; the submission workflow + turns the file into an LFS object when it moves it into `data/`. + +### For contributors + +- **Submitting a new dataset:** nothing special is required — stage your file at + the repository root and open a PR (see [CONTRIBUTING.md](CONTRIBUTING.md) and + the + [Submission Workflow](https://docs.open-reaction-database.org/en/latest/submissions.html)). +- **Editing a file that already lives under `data/` from a fork:** that file is + an LFS object, so point LFS uploads at your own fork once before pushing (you + cannot write to the canonical repository's LFS store): + + ```bash + git config lfs.pushurl https://github.com//ord-data.git/info/lfs + ``` + +### For maintainers (CI) + +Freshly pushed objects are not on the Hugging Face mirror until the post-merge +mirror job runs, so CI and the mirror override the read endpoint back to GitHub +at runtime (`git config lfs.url …`): + +- [`validation.yml`](.github/workflows/validation.yml) pulls only each matrix + shard's objects from GitHub, sparsely, instead of the whole dataset in every + job. +- [`submission.yml`](.github/workflows/submission.yml) reads from GitHub so fork + and branch submissions are validated before their bytes reach Hugging Face. +- [`huggingface_mirror.yml`](.github/workflows/huggingface_mirror.yml) reads the + to-be-mirrored objects from GitHub. + +## Contributing + +Please see the [Submission Workflow](https://docs.open-reaction-database.org/en/latest/submissions.html) documentation. Make sure to review the [license](https://github.com/open-reaction-database/ord-data/blob/main/LICENSE) and [terms of use](https://github.com/open-reaction-database/ord-data/blob/main/CONTRIBUTING.md#terms-of-use). + +## Maintainer notes + +### Skipping the `Update submission` step + +The submission workflow's `Update submission` step runs +[`scripts/process_dataset.py`](scripts/process_dataset.py) `--update --cleanup` +to assign reaction/dataset IDs and timestamps to newly +submitted files and rewrite them to the canonical on-disk format. For +maintainer PRs that touch dataset files but should *not* be re-processed +this way — e.g., format conversions or mass migrations of already-finalized +data — apply the `skip-update-submission` label to the PR. Note that the +label leaves such a PR with no dataset validation inside the submission +workflow: `Validate submission` runs only for fork PRs and for this +workflow's own re-runs, so on a labeled maintainer PR both steps sit out. +The corpus sweep in [`validation.yml`](.github/workflows/validation.yml) +covers the result on merge to `main`. + +### Converting datasets to Parquet + +Published datasets are stored as Parquet only, and new submissions are written +that way by `process_dataset.py`, so `data/` holds no `.pb.gz` to convert. +[`scripts/convert_to_parquet.py`](scripts/convert_to_parquet.py) handles the +case where one lands there anyway: it globs `data/*/ord_dataset-*.pb.gz`, +converts each 1:1 (carrying the existing `dataset_id`), and refuses to overwrite +an existing output whose reaction count disagrees with its input. Converting the +corpus is this script's job, not a side effect of editing one dataset, which is +why `process_dataset.py` leaves an edited file in whatever format it has. + +It needs `ord_schema`, which comes from the `pipeline` dependency group. Because +it reads `.pb.gz` content, pull the inputs first. With `data/` Parquet-only the +converter has nothing to do and says so — these steps are worth running only +once a `.pb.gz` has actually appeared: + +```bash +uv sync --only-group pipeline + +git lfs pull --include="data/*/ord_dataset-*.pb.gz" +uv run --no-sync python scripts/convert_to_parquet.py --dry-run # preview +uv run --no-sync python scripts/convert_to_parquet.py +git rm data/*/*.pb.gz # keep only the Parquet versions +``` + +Commit the new `.parquet` files (they become LFS objects), push them (see +[Pushing new LFS objects](#pushing-new-lfs-objects)), and open the PR with the +`skip-update-submission` label. Validation runs against the full dataset on +merge to `main`. + +### Pushing new LFS objects + +[`.lfsconfig`](.lfsconfig) routes LFS **reads** to the Hugging Face mirror and +deliberately sets no `pushurl`, so a plain push would try to upload new objects +to HF — which you cannot write. Point LFS uploads at GitHub for the push, and +make sure git can authenticate to `github.com` over **HTTPS** for the LFS API +(the LFS endpoint is HTTPS even when your `git` remote is SSH). The simplest +auth is the GitHub CLI: + +```bash +git config lfs.pushurl https://github.com/open-reaction-database/ord-data.git/info/lfs +gh auth setup-git # let git use your gh token for github.com over HTTPS +git push -u origin +``` + +Or, as a one-off without persisting any config: + +```bash +git -c lfs.pushurl=https://github.com/open-reaction-database/ord-data.git/info/lfs \ + -c 'credential.https://github.com.helper=!gh auth git-credential' \ + push -u origin +``` + +Reads stay on the mirror; only your uploads go to GitHub. On merge to `main`, +`huggingface_mirror.yml` copies the new objects to Hugging Face. + +## License + +This repository carries two licenses, because it holds both data and code: + +| what | license | file | +| --- | --- | --- | +| The datasets under `data/` (and the repository metadata describing them) | [CC-BY-SA-4.0](LICENSE) | `LICENSE` | +| The code under `scripts/` and `.github/` | [Apache-2.0](LICENSE-CODE) | `LICENSE-CODE` | + +If you are using ORD data, CC-BY-SA-4.0 is the license that applies to you; it +is what `CITATION.cff` and the [Hugging Face +mirror](https://huggingface.co/datasets/open-reaction-database/ord-data) declare. + +The code carries a separate license because Creative Commons licenses are not +intended for software — [Creative Commons recommends against +it](https://creativecommons.org/faq/#can-i-apply-a-creative-commons-license-to-software) +— and because the project's other code repositories, including +[ord-schema](https://github.com/Open-Reaction-Database/ord-schema), are +Apache-2.0. + +## Citation + +If you use this dataset, please cite the Open Reaction Database paper: + +```bibtex +@article{kearnes2021ord, + author = {Kearnes, Steven M. and Maser, Michael R. and Wleklinski, Michael and Kast, Anton and Doyle, Abigail G. and Dreher, Spencer D. and Hawkins, Joel M. and Jensen, Klavs F. and Coley, Connor W.}, + title = {The Open Reaction Database}, + journal = {Journal of the American Chemical Society}, + year = {2021}, + volume = {143}, + number = {45}, + pages = {18820--18826}, + doi = {10.1021/jacs.1c09820}, +} +``` diff --git a/data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.parquet b/data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.parquet new file mode 100644 index 0000000000000000000000000000000000000000..bea988d0c4557eb96b137a05dd9546dcb08a96bc --- /dev/null +++ b/data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:bf1686ca6edac300a61acb5a5ee006ab5fd61007962ae19062b3d3c7879f84a9 +size 274285 diff --git a/data/03/ord_dataset-0316886541d9435489859c2ad7edc863.parquet b/data/03/ord_dataset-0316886541d9435489859c2ad7edc863.parquet new file mode 100644 index 0000000000000000000000000000000000000000..a8a79e9601668bad4a3fe154c4616be923a217b6 --- /dev/null +++ b/data/03/ord_dataset-0316886541d9435489859c2ad7edc863.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:786b10eb7815c92e07800b7005fbdd046f15158c834b05596c6b02d3d6d2128e +size 24703 diff --git a/data/0c/ord_dataset-0c75d67751634f0594b24b9f498b77c2.parquet b/data/0c/ord_dataset-0c75d67751634f0594b24b9f498b77c2.parquet new file mode 100644 index 0000000000000000000000000000000000000000..f60f7ec0cb6b589930ae2761d6a705fe68f9e142 --- /dev/null +++ b/data/0c/ord_dataset-0c75d67751634f0594b24b9f498b77c2.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:00fe35e881dc9a02feaa9186eaf69a221a44f1a281ea1b01f593953ecd65ede6 +size 29842 diff --git a/data/10/ord_dataset-10b940e7982c4622b1e1ac879394aba6.parquet b/data/10/ord_dataset-10b940e7982c4622b1e1ac879394aba6.parquet new file mode 100644 index 0000000000000000000000000000000000000000..802e2a32850317caeddce7a64815f02d5301c48d --- /dev/null +++ b/data/10/ord_dataset-10b940e7982c4622b1e1ac879394aba6.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:79923835d81b529c5d771cd7dc0ad6707348e6ceecbe4528205c47bb6de1d044 +size 43989 diff --git a/data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet b/data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet new file mode 100644 index 0000000000000000000000000000000000000000..2109bb0c327cbb21c641d88f1db54c757c7b577c --- /dev/null +++ b/data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:d0fa5e21c621d16714bae1b9157022b5a3ea02db909a2af8d7b5b976f7c950b5 +size 1112719074 diff --git a/data/17/ord_dataset-172039a759a440219a68af62d203b79b.parquet b/data/17/ord_dataset-172039a759a440219a68af62d203b79b.parquet new file mode 100644 index 0000000000000000000000000000000000000000..5cabdf232061b7ce8159071358d00eb1120508b7 --- /dev/null +++ b/data/17/ord_dataset-172039a759a440219a68af62d203b79b.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:e32594d22839eaae4554642845e4e9dfc6abcf4bcecece6b26f4be64ce3bf39c +size 21417 diff --git a/data/1d/ord_dataset-1d3a1a6fb70d46c084602d0688967afc.parquet b/data/1d/ord_dataset-1d3a1a6fb70d46c084602d0688967afc.parquet new file mode 100644 index 0000000000000000000000000000000000000000..131153d42ba14130f2f5634dacb0765fec79302e --- /dev/null +++ b/data/1d/ord_dataset-1d3a1a6fb70d46c084602d0688967afc.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:9351ed4883b04c23505e6a1e8a3e216f90b7b79fd1ca72fd18f33c33a94e71b2 +size 11740 diff --git a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.parquet b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.parquet new file mode 100644 index 0000000000000000000000000000000000000000..a1bf22b7b8c45563cc24b21bbb4062c704d64836 --- /dev/null +++ b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:b1fd81bb3034644117b7d07e0471ede7370597bb4bd2433dd4b5c20bf02fad99 +size 99755 diff --git a/data/20/ord_dataset-2038a3c967db4a32a8fbce288437e929.parquet b/data/20/ord_dataset-2038a3c967db4a32a8fbce288437e929.parquet new file mode 100644 index 0000000000000000000000000000000000000000..a2c02f8f8fa76faf783a305a8dac246dba219887 --- /dev/null +++ b/data/20/ord_dataset-2038a3c967db4a32a8fbce288437e929.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:52dd1e2d44ff052592a9f78bd5c9aac454ad90ab7a7f2f9795c4e742f89644d3 +size 17627 diff --git a/data/2b/ord_dataset-2be11f57f3304e678ea8469baf6dd1bc.parquet b/data/2b/ord_dataset-2be11f57f3304e678ea8469baf6dd1bc.parquet new file mode 100644 index 0000000000000000000000000000000000000000..8fd0cdb6693c1922f744107f38af01615fe2f24c --- /dev/null +++ b/data/2b/ord_dataset-2be11f57f3304e678ea8469baf6dd1bc.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:c7d17ab4af3551a4b2883c6e18c1f3a49b6c19d30d37fad762802aeeb275d948 +size 112943 diff --git a/data/2b/ord_dataset-2be30f5d8dcd471aa6ad410bdee05902.parquet b/data/2b/ord_dataset-2be30f5d8dcd471aa6ad410bdee05902.parquet new file mode 100644 index 0000000000000000000000000000000000000000..92d68627476358c6de6e961ffb58db8b73badf5d --- /dev/null +++ b/data/2b/ord_dataset-2be30f5d8dcd471aa6ad410bdee05902.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:6846bf47bd0d9652d1164f1dbc65cf730502e117131778499b8a10a98ef828b7 +size 17947 diff --git a/data/31/ord_dataset-31989f1b2b9d4885b1dd2d9982da4517.parquet b/data/31/ord_dataset-31989f1b2b9d4885b1dd2d9982da4517.parquet new file mode 100644 index 0000000000000000000000000000000000000000..b6a7b5d212b2f91329c14498f8c1413654fec600 --- /dev/null +++ b/data/31/ord_dataset-31989f1b2b9d4885b1dd2d9982da4517.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:60f4f1bf9fd81166ce59e3ad8915310b0af5bca13956cab3b331748c1d3194dd +size 17258 diff --git a/data/35/ord_dataset-35a5a513f1dd44a3a97c88da99f81a00.parquet b/data/35/ord_dataset-35a5a513f1dd44a3a97c88da99f81a00.parquet new file mode 100644 index 0000000000000000000000000000000000000000..0271cefdcf0b3bcfb4bec008b85963a1806aa3a5 --- /dev/null +++ b/data/35/ord_dataset-35a5a513f1dd44a3a97c88da99f81a00.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:59f2cdd054631bde7354e21fc7080f0b80ebf2b5379f8ccd78b2df79d86b25d8 +size 19743 diff --git a/data/3b/ord_dataset-3b5db90e337942ea886b8f5bc5e3aa72.parquet b/data/3b/ord_dataset-3b5db90e337942ea886b8f5bc5e3aa72.parquet new file mode 100644 index 0000000000000000000000000000000000000000..5f08fdf1677d312b090bdde3e8abda2e0d7bff36 --- /dev/null +++ b/data/3b/ord_dataset-3b5db90e337942ea886b8f5bc5e3aa72.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:fce2d70c28db7100b3ca5c3f298484daf4c4043c11a18da066db16ad2e36012c +size 43118 diff --git a/data/3b/ord_dataset-3b8a2ef300e145468579027f206a3ac8.parquet b/data/3b/ord_dataset-3b8a2ef300e145468579027f206a3ac8.parquet new file mode 100644 index 0000000000000000000000000000000000000000..7484bcbd34f6f9e9ca71cc9e9863246664873ea8 --- /dev/null +++ b/data/3b/ord_dataset-3b8a2ef300e145468579027f206a3ac8.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:f8438f4490541ecd38d92208decc48ff33424d52772cc42701b7eb886fc14b8a +size 184557 diff --git a/data/46/ord_dataset-46ff9a32d9e04016b9380b1b1ef949c3.parquet b/data/46/ord_dataset-46ff9a32d9e04016b9380b1b1ef949c3.parquet new file mode 100644 index 0000000000000000000000000000000000000000..2dbe07c057fa5631c66c9584110ddfa79f1549af --- /dev/null +++ b/data/46/ord_dataset-46ff9a32d9e04016b9380b1b1ef949c3.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:39440ea3e5442dddbb4daccbc48fb53940724085327c0e3b82909e1fd8cc661a +size 395126 diff --git a/data/47/ord_dataset-47eaacc46c3a4487bbdf99adb1a15e41.parquet b/data/47/ord_dataset-47eaacc46c3a4487bbdf99adb1a15e41.parquet new file mode 100644 index 0000000000000000000000000000000000000000..459e93d3f7d719aad3eb137a69480cd53aa0cfae --- /dev/null +++ b/data/47/ord_dataset-47eaacc46c3a4487bbdf99adb1a15e41.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:7e09c98aa540e15d44959f03028590278bf508650950778568fd264d3a7535c4 +size 8261981 diff --git a/data/48/ord_dataset-488402f6ec0d441ca2f7d6fabea7c220.parquet b/data/48/ord_dataset-488402f6ec0d441ca2f7d6fabea7c220.parquet new file mode 100644 index 0000000000000000000000000000000000000000..02a86cd29573dd0aeb474be7cd556e873a40b832 --- /dev/null +++ b/data/48/ord_dataset-488402f6ec0d441ca2f7d6fabea7c220.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:d1b658a9ed389f226baa003488c226fbd00dc35c44fc8e5029ef74b030928788 +size 10249187 diff --git a/data/4d/ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6.parquet b/data/4d/ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6.parquet new file mode 100644 index 0000000000000000000000000000000000000000..4d3a915fec94c8c0adb43b95f1a61673abd7475f --- /dev/null +++ b/data/4d/ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:be51ac3256a9f6793893bd59878f44f223f50ad530a1f71da0c408abf36ef70a +size 17114 diff --git a/data/4d/test-pbtxt.pbtxt b/data/4d/test-pbtxt.pbtxt new file mode 100644 index 0000000000000000000000000000000000000000..3c35bbd474f4c315b567a8eaeba59a075213896e --- /dev/null +++ b/data/4d/test-pbtxt.pbtxt @@ -0,0 +1,26373 @@ +name: "Figure 4 from Chemistry informer libraries" +description: "Reactions from Kutchukian et al. Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods. Chem. Sci., 2016,7, 2604-2613; https://doi.org/10.1039/C5SC04751J" +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 30.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-ff7a068e31cf4af1a1410cca4024bc84" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 33.88 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-37be7814305b45af80c6a17f7cc72c15" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 23.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-99b7071ffced43b894b9fac46551019d" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 24.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3a7e4f719e214c809880b554af195467" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 1.38 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-2dde4fbb8ce04bc181a682a7557abc71" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 41.08 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-005c6ae9ab9c492aa38e443b2fc48281" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-bdbd347491d940ddade73c21da6cc8a4" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 54.2 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-e1e8040376254ffbb48ef245fa505172" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-04819e73915045bf989adc7b07500dad" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-035e2da461954e20b37873ae1b1bd246" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3783b54621c94be6b9e81e30acbe7ff6" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 28.908 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-55fd6482d44345e78bf3941372bba8a1" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-429743da704c4203a5d67857898e0a49" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 39.96 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-a997bf0c4472451b8322e07f319ce5b0" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 78.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-8b251336273640e0a79746bfb44e35ca" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-84d1d8da73f246249fe3d38f09ba138b" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3997680b0fb14c80a41342a2766f1f70" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "Cc1cccc(c1NC(=O)C(=O)O)C" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-0c313e5b459747298e8f31db526b1845" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 1.63 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-5ecfcb9f6b3f4008841d5a438e4e7ca7" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 30.8 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-b68f660254ae484aa96d90cb2bbf21e0" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 78.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-5502e98555624e3f9c60c91ceda923f6" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 33.6 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-b6f150c99f064d29b6017db73cb2f541" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 2.53 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-145481f142da49ed99fa5db44ecd9c88" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 50.56 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-b04ffc62e9d3403599612a4d5f0088af" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-f2d9d96d66da4af3ac6fd4662faea797" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 16.26 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-d1ba573d7db945b4bcdcfa26a7d96c05" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-c6809fff1a4d4101ac7acafdb40200ec" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-7fa9853f720e4f329be404ac8b49c413" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-9ed71a47ea1042179794fae5970bad75" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 32.472 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-1e9819fc13134d6388708454c61c4d78" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-b30dcea4b6d347d6ae03f7ec44eead0b" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 6.66 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-834036b549d541259f77dc86bbef5d35" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 81.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-70258eeba5f24053a274569f19e16592" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-8a830fbdced240348666e75985bb08ec" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-44f82dbcbc8f4edb962d35d4d12e7ecb" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "COc1cccc(c1NC(=O)C(=O)O)OC" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-5876661e31e24b0c816e513c647ba7d3" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 22.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-92448a739c8e482b8aadc7b2e03d7ac8" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 49.28 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-75be42c3f9fc406a8c61cdd44bcd8ec9" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-0cfdeed5fd334170bf6832a36a1ad50a" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 52.8 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-e6faadf0d50a45b2bef77fd6e6b74bba" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 1.15 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-cac77f2c62964a17b279ea120addfe15" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 66.36 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-c43a52595d694bf59a6f4a46685510a6" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-b835f77514d347eabdc375288580ce9e" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 43.36 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-8f1c477cdd4042f996c6bcfc0cdb2760" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3a7b0c8e219743b8883d0af70cbaef8a" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-4ad3d69b8a8a496198d6b1b75a00a808" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-8b80e81445364184a2a17f9f21689da8" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 19.8 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-a4b8a772ccf34a5a93ee9eca84dd89bf" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-96459c00fd7646499261749ea36912da" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 59.94 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-695a9d94c4bb41a9b84e7441694c4984" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 78.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-caad139eb285462784a3403b80fcd080" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3cdc650efb71406dba96432e9a6b9920" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-a03d4aa48d9f4b38b972e51bdd79ad4b" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-389573e347664eacbbbfa9d4ed5e4513" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 39.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-4f9dfedd89b643b1b70fa5edbc901af4" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 52.36 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-e127d32640c34f94bea9bf3e8dedb5cc" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 7.8 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-a6a1661c85f6470bb1c55ba2ff78546a" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 38.4 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-4177e93cc9cc405c9e9282e8535fbefd" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-daa34755458f449a837d64447482e24a" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 60.04 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-6656a4308ace417195d8e20cc0f186af" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-25f4511e384a4be59c632e62f0425ebc" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 27.1 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-83489e97b0fa44a493d7cb9414307085" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-ec2f5e230a574fa4a0d55fe2b4c8d237" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-164d2a7162764ce7aeaa4e2ada8f6f4d" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3081234d5d914c89b725d53d9ac7a7c6" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 8.316 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-5d5bd9c748bf4ebe9ae402b770e86286" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-b1360f0587454b2ba1dad8ec6aefc128" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 6.66 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-e47131e32b1c4e33a9a3c689c03d31bc" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 80.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-bf8b93603f064618a108bea60beae8cb" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-bcf48df8c67d4a9886c76fec992f508f" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-7b3a4301337947dc83bdfb1378bbba71" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3410257fd5e047ebb257919e7156dc1d" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 2.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-5657c90b4fed4903a8cce5a90b4a2167" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 40.04 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-f90332a889204e0f95b82d1883469001" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 15.6 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-7314f4d46d7e42f98083f8f49240c053" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 28.8 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-4fd429148952418bab997523b8350b08" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-5f843d22199b4124a57fff450dd26ce2" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 47.4 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-9ff3e57ef25e4008aff47932ebba023c" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-3fd92afbd3f54f2f8c1c2ac1992d74e6" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 54.2 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-1c138e96a2b24504ba0efafe6c27aa30" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-038d03b9e7724f70a68da7ffe3dddd07" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-2ecbbbb182354f8c9c95ea76b66d6ff2" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-e74c70aae3f845fd9b4800faef593473" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-692250ef62f546489a5b9f8931868e19" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-af8231249442440d834de5d07aaf8d2a" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 6.66 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-9b23b4cf9b76496b806d158883e480da" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 61.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-09ad07959c3148449917ba0e772ef309" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-1b37d119057a4837befd6d13fcb25897" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-e5183177929d4254bdc9df3323b5069b" +} +reactions { + inputs { + key: "Amine" + value { + components { + identifiers { + type: SMILES + value: "C1CCNCC1" + } + amount { + moles { + value: 3.75 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 7.5 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "[Cu]I" + } + amount { + moles { + value: 0.25 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + } + } + inputs { + key: "Aryl Halide" + value { + components { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4" + } + amount { + moles { + value: 2.5 + units: MICROMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + addition_order: 1 + } + } + inputs { + key: "Catalyst" + value { + components { + identifiers { + type: SMILES + value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CS(=O)C" + } + amount { + volume { + value: 12.5 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + } + } + setup { + vessel { + type: WELL_PLATE + details: "96 Glass Vials" + material { + type: GLASS + } + volume { + value: 250.0 + units: MICROLITER + } + } + environment { + type: GLOVE_BOX + details: "Nitrogen Filled" + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 80.0 + units: CELSIUS + } + } + stirring { + type: STIR_BAR + details: "Magnetic Stir Bar" + } + } + workups { + type: ADDITION + details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously." + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CS(C)=O" + } + amount { + volume { + value: 95.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC(=O)O" + } + amount { + volume { + value: 5.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: NAME + value: "1,3,5-trimethoxybenzene" + } + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 0.5 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + } + } + workups { + type: ALIQUOT + details: "25 microliter of resulting solution is taken" + amount { + volume { + value: 25.0 + units: MICROLITER + } + } + } + workups { + type: ADDITION + details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis" + input { + components { + identifiers { + type: SMILES + details: "NAME resolved by the PubChem API" + value: "CC#N" + } + amount { + volume { + value: 700.0 + units: MICROLITER + } + } + reaction_role: WORKUP + } + } + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5" + } + is_desired_product: true + measurements { + analysis_key: "UPLC-MS" + type: YIELD + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "UPLC-MS" + value { + type: LCMS + details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)" + instrument_manufacturer: "Waters" + } + } + } + provenance { + experimenter { + name: "Spencer Dreher" + orcid: "0000-0002-5094-1218" + organization: "Merck" + email: "spencer_dreher@merck.com" + } + city: "Rahway, NJ" + doi: "10.1039/C5SC04751J" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract" + record_created { + time { + value: "6/2/2021, 8:10:58 AM" + } + person { + name: "Michael Wleklinski" + orcid: "0000-0001-6735-4696" + organization: "Merck" + email: "michael.wleklinski@merck.com" + } + } + record_modified { + time { + value: "Wed Jul 7 21:27:17 2021" + } + person { + username: "github-actions" + email: "github-actions@github.com" + } + details: "Automatic updates from the submission pipeline." + } + } + reaction_id: "ord-9785e38ceca74e4c83d6aeca79400a0e" +} +dataset_id: "ord_dataset-4d431564f3ef4e9c91d8da5836f4eae6" diff --git a/data/52/ord_dataset-52bd3b0ec72c443aab113bcea09bf3f4.parquet b/data/52/ord_dataset-52bd3b0ec72c443aab113bcea09bf3f4.parquet new file mode 100644 index 0000000000000000000000000000000000000000..fa9c32394914f659fa5686819a44f917701347ff --- /dev/null +++ b/data/52/ord_dataset-52bd3b0ec72c443aab113bcea09bf3f4.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:e3bf70610705d361b92b40c09ceaffff3d4f66002e958e5ea9c47bba9095297a +size 10583 diff --git a/data/54/ord_dataset-5415f83da68e4797856ddd330dda5c61.parquet b/data/54/ord_dataset-5415f83da68e4797856ddd330dda5c61.parquet new file mode 100644 index 0000000000000000000000000000000000000000..4743f1e6b43642075e144e7c17fead1b5f2718cd --- /dev/null +++ b/data/54/ord_dataset-5415f83da68e4797856ddd330dda5c61.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:a186a7a7264e94fd958787a5a6a9d810e9c9c00608f1c6e136416098c39a2165 +size 25251 diff --git a/data/54/ord_dataset-5481550056a14935b76e031fb94b88be.parquet b/data/54/ord_dataset-5481550056a14935b76e031fb94b88be.parquet new file mode 100644 index 0000000000000000000000000000000000000000..3c650f16fe90a2da0f2da730496f7583baaa90f0 --- /dev/null +++ b/data/54/ord_dataset-5481550056a14935b76e031fb94b88be.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:48508c30931b04b4fe2e3bee55b84c83d10f57578c1ed5ccddbfb81875575702 +size 7666127 diff --git a/data/55/ord_dataset-5540e162c09f4c04905ddc8ba9c931c6.parquet b/data/55/ord_dataset-5540e162c09f4c04905ddc8ba9c931c6.parquet new file mode 100644 index 0000000000000000000000000000000000000000..f64dfe6a37b48b00e46cb86354c67f8b2f4542be --- /dev/null +++ b/data/55/ord_dataset-5540e162c09f4c04905ddc8ba9c931c6.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:7e44b014c9041d86e00bc4fb4b70b3c6b3b94c0e35634467ace02c330efcd1a4 +size 13289 diff --git a/data/55/ord_dataset-55de08a995554f558c25fc43eac62359.parquet b/data/55/ord_dataset-55de08a995554f558c25fc43eac62359.parquet new file mode 100644 index 0000000000000000000000000000000000000000..5e20ed1af13fa56d45016ec3ed9be33a5a9e2de9 --- /dev/null +++ b/data/55/ord_dataset-55de08a995554f558c25fc43eac62359.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:9e4c3fefafe68d6cb43d5a39b8c441f440ce0c4626abbbe695c922089557b0f7 +size 11719 diff --git a/data/5c/ord_dataset-5c9a10329a8a48968d18879a48bb8ab2.parquet b/data/5c/ord_dataset-5c9a10329a8a48968d18879a48bb8ab2.parquet new file mode 100644 index 0000000000000000000000000000000000000000..0b879178e7b305416e32bd82e59d18e7790fecf9 --- /dev/null +++ b/data/5c/ord_dataset-5c9a10329a8a48968d18879a48bb8ab2.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:a2ea1363cb895b590ae765e918f98f90d243d6caba763ed74543ae62e503b0b0 +size 712770 diff --git a/data/5e/ord_dataset-5e8318f0dda04b398c14f4c3adfeb32c.parquet b/data/5e/ord_dataset-5e8318f0dda04b398c14f4c3adfeb32c.parquet new file mode 100644 index 0000000000000000000000000000000000000000..b2fb8240c43c567594d0e9af800f8d3198c641a4 --- /dev/null +++ b/data/5e/ord_dataset-5e8318f0dda04b398c14f4c3adfeb32c.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:94de6b8e87229d5db4fe8c17212afa2d3563478ca32aee934cc449559cab0bca +size 8027 diff --git a/data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet b/data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet new file mode 100644 index 0000000000000000000000000000000000000000..146f82c8ea6a95683c62d93fa6bd4e542fce4402 --- /dev/null +++ b/data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:2f478e163ab9f9ee2f001172fc9f0c33b0a65ec2dc787c12298f6e85bc86f7a6 +size 11134 diff --git a/data/67/ord_dataset-675eddcaa6674ce3ae61e79bbc1e1c08.parquet b/data/67/ord_dataset-675eddcaa6674ce3ae61e79bbc1e1c08.parquet new file mode 100644 index 0000000000000000000000000000000000000000..e83b583d09a532df2241073d77e5e3da599701b2 --- /dev/null +++ b/data/67/ord_dataset-675eddcaa6674ce3ae61e79bbc1e1c08.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:1ecc5469785e55997f244eb5f8d6dbc78029cbb233bd6a140b5f02d5d01860a1 +size 114800 diff --git a/data/68/ord_dataset-68cb8b4b2b384e3d85b5b1efae58b203.parquet b/data/68/ord_dataset-68cb8b4b2b384e3d85b5b1efae58b203.parquet new file mode 100644 index 0000000000000000000000000000000000000000..db38d0d1b7e2cff52b00d29550193e12c87a5322 --- /dev/null +++ b/data/68/ord_dataset-68cb8b4b2b384e3d85b5b1efae58b203.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:36cea7705307a5e359a176ed3862994e3edc60ae4363fc2f3c5862affff6bb21 +size 419710 diff --git a/data/6a/ord_dataset-6a0bfcdf53a64c07987822162ae591e2.parquet b/data/6a/ord_dataset-6a0bfcdf53a64c07987822162ae591e2.parquet new file mode 100644 index 0000000000000000000000000000000000000000..b7edb231b06b69c1bef2fbc1594099c6fe8f37ec --- /dev/null +++ b/data/6a/ord_dataset-6a0bfcdf53a64c07987822162ae591e2.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:f970251d44ad75b68c8f6b8f3f28ff97f540fb7967d3bbc9b7338a7d7290ed3a +size 16175 diff --git a/data/7a/ord_dataset-7acd6ad2bf4d4cff841cad008ab726d5.parquet b/data/7a/ord_dataset-7acd6ad2bf4d4cff841cad008ab726d5.parquet new file mode 100644 index 0000000000000000000000000000000000000000..6fa92e72f32e253dd9fda36e7b04636886f61362 --- /dev/null +++ b/data/7a/ord_dataset-7acd6ad2bf4d4cff841cad008ab726d5.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:b6dfe8e151a396c5332668c015bce764d23c667240e443495990205c66e4a1e5 +size 72692 diff --git a/data/7d/ord_dataset-7d8f5fd922d4497d91cb81489b052746.parquet b/data/7d/ord_dataset-7d8f5fd922d4497d91cb81489b052746.parquet new file mode 100644 index 0000000000000000000000000000000000000000..28b42b133cb3ef5c195494d634a56a1824e24ec3 --- /dev/null +++ b/data/7d/ord_dataset-7d8f5fd922d4497d91cb81489b052746.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:3d657d1eda5703b58b627565894890269b50b18e987709e70fd7968d83e59101 +size 194483 diff --git a/data/80/ord_dataset-805ad863feef48579d95d86a728035f4.parquet b/data/80/ord_dataset-805ad863feef48579d95d86a728035f4.parquet new file mode 100644 index 0000000000000000000000000000000000000000..2a0ad5a9496526c80f07070cecc723fc6f229379 --- /dev/null +++ b/data/80/ord_dataset-805ad863feef48579d95d86a728035f4.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:31b7c4762145e5dad973050373cd967bdd85caf3a9858767c83a17fed6c4af36 +size 5088296 diff --git a/data/89/ord_dataset-89b083710e2d441aa0040c361d63359f.parquet b/data/89/ord_dataset-89b083710e2d441aa0040c361d63359f.parquet new file mode 100644 index 0000000000000000000000000000000000000000..754176f8409c383f71d7b4f33aa91dd57a8ad859 --- /dev/null +++ b/data/89/ord_dataset-89b083710e2d441aa0040c361d63359f.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:9a5cbdae282df3da7249e7525b7ecb739e4892061abe1f66e62c3fd69736ad72 +size 21940 diff --git a/data/8c/test-8c36.pb b/data/8c/test-8c36.pb new file mode 100644 index 0000000000000000000000000000000000000000..e71e205f827dccc14aa68a28a4a56a3fa2a2b6cc --- /dev/null +++ b/data/8c/test-8c36.pb @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:ca0464d32c6ab2904f5f40d0e3837f049e73df6847b1d68973c32d59f7e9d4e8 +size 3938 diff --git a/data/8c/test-a8ad.pb b/data/8c/test-a8ad.pb new file mode 100644 index 0000000000000000000000000000000000000000..08f427da16b3d870bfb0ffebe9996c58424b004b --- /dev/null +++ b/data/8c/test-a8ad.pb @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:80f96f574f2d310645483ea44f230aa24d0a505cea5fce7bc8d400c8f95d5333 +size 5237 diff --git a/data/8c/test-c503.pb b/data/8c/test-c503.pb new file mode 100644 index 0000000000000000000000000000000000000000..16ec416fec2e86e85211b8b8488ace045c6006ce --- /dev/null +++ b/data/8c/test-c503.pb @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:d3905106f3ed3d329493df8e4e0ba19546a0fc0db3dd49582c4890b0a8aad15b +size 5014 diff --git a/data/8c/test.pb b/data/8c/test.pb new file mode 100644 index 0000000000000000000000000000000000000000..e71e205f827dccc14aa68a28a4a56a3fa2a2b6cc --- /dev/null +++ b/data/8c/test.pb @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:ca0464d32c6ab2904f5f40d0e3837f049e73df6847b1d68973c32d59f7e9d4e8 +size 3938 diff --git a/data/8d/ord_dataset-8d1e28ec1f6b4ee8ad372e0b5ed7a62e.parquet b/data/8d/ord_dataset-8d1e28ec1f6b4ee8ad372e0b5ed7a62e.parquet new file mode 100644 index 0000000000000000000000000000000000000000..7dd92016389a284a041beefd7c721a6706fbbc39 --- /dev/null +++ b/data/8d/ord_dataset-8d1e28ec1f6b4ee8ad372e0b5ed7a62e.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:e4f7505229e29321b5615f32ec2edcf45c9bc531bee2810d2a8985319b7ee127 +size 20904 diff --git a/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet b/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet new file mode 100644 index 0000000000000000000000000000000000000000..17f2d793caf44874e1385d8aead4146d913ed313 --- /dev/null +++ b/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa +size 210626 diff --git a/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet b/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet new file mode 100644 index 0000000000000000000000000000000000000000..21e075c2edcb6700e32a1a1f53e3e22023cf51d5 --- /dev/null +++ b/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:195765643b4aaad79d9ed82de6737a4855b9f2716e0bc0aa10cff950b7604d39 +size 126909 diff --git a/data/a1/ord_dataset-a12fa15d036d489c971b0b514caeae52.parquet b/data/a1/ord_dataset-a12fa15d036d489c971b0b514caeae52.parquet new file mode 100644 index 0000000000000000000000000000000000000000..965a688401b5c1f8306093891f041a5930422ff8 --- /dev/null +++ b/data/a1/ord_dataset-a12fa15d036d489c971b0b514caeae52.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:ea52ef52e2ecf3eb33d74ca3ffac14ef539357551d252fbc706e95f60c94fca6 +size 39322 diff --git a/data/ac/ord_dataset-ac78456835404910b3a4c840248b6ac9.parquet b/data/ac/ord_dataset-ac78456835404910b3a4c840248b6ac9.parquet new file mode 100644 index 0000000000000000000000000000000000000000..46b1811f291a9ae1c019ee224f6c3ea6f0d49063 --- /dev/null +++ b/data/ac/ord_dataset-ac78456835404910b3a4c840248b6ac9.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:52a9d0084abc051a792bfb71501af03ec13bdabc24a7db4e33b7223ddf8c884c +size 126388 diff --git a/data/b4/ord_dataset-b440f8c90b6343189093770060fc4098.parquet b/data/b4/ord_dataset-b440f8c90b6343189093770060fc4098.parquet new file mode 100644 index 0000000000000000000000000000000000000000..53492834dcb5b86e8ec8963d509846b4c7b58391 --- /dev/null +++ b/data/b4/ord_dataset-b440f8c90b6343189093770060fc4098.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:d289e2e9fbb77df61faadeb65cfadfbee0216b05a7d209b3ae3b3aca04a9993a +size 111495 diff --git a/data/bc/ord_dataset-bc349c19b4384756a2aee8aa525b6c2a.parquet b/data/bc/ord_dataset-bc349c19b4384756a2aee8aa525b6c2a.parquet new file mode 100644 index 0000000000000000000000000000000000000000..251432118dc03e4f89175c811370c8206528db2e --- /dev/null +++ b/data/bc/ord_dataset-bc349c19b4384756a2aee8aa525b6c2a.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:d4dbdaba59ac728696dea5bc0cafed5c5ab3236cc37da6e29b73e8a792f3b4a3 +size 17150 diff --git a/data/c5/ord_dataset-c5b00523487a4211a194160edf45e9ab.parquet b/data/c5/ord_dataset-c5b00523487a4211a194160edf45e9ab.parquet new file mode 100644 index 0000000000000000000000000000000000000000..6e8ea0ab39c735ee119634eec35429550e36b513 --- /dev/null +++ b/data/c5/ord_dataset-c5b00523487a4211a194160edf45e9ab.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:73c04ce2acaf6cf2b6b3ecda8c623d2a321435f1f5830aedb0a0f1afd562bdc4 +size 179304 diff --git a/data/c7/ord_dataset-c703268ea43a4c7e802c6048b6166b34.parquet b/data/c7/ord_dataset-c703268ea43a4c7e802c6048b6166b34.parquet new file mode 100644 index 0000000000000000000000000000000000000000..5861ffe73c9b0ed244e0d8066186895029503a83 --- /dev/null +++ b/data/c7/ord_dataset-c703268ea43a4c7e802c6048b6166b34.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:159472bff84a548cb2def33ae92ff36c27139271372e38e70bba8eea152760d3 +size 16939 diff --git a/data/cb/ord_dataset-cbcc4048add7468e850b6ec42549c70d.parquet b/data/cb/ord_dataset-cbcc4048add7468e850b6ec42549c70d.parquet new file mode 100644 index 0000000000000000000000000000000000000000..4c76c427a708f790793510e30b8c4baa66666a38 --- /dev/null +++ b/data/cb/ord_dataset-cbcc4048add7468e850b6ec42549c70d.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:fd62fb8331a5d2d68337882bd711d04f085b6beec7ef1283945f7f72a8cefb81 +size 30311 diff --git a/data/ce/ord_dataset-ce5045aceb214cfc8bfd0ef3031e2737.parquet b/data/ce/ord_dataset-ce5045aceb214cfc8bfd0ef3031e2737.parquet new file mode 100644 index 0000000000000000000000000000000000000000..fc43b2a6f49c4c739addbb027fa158692dee47ea --- /dev/null +++ b/data/ce/ord_dataset-ce5045aceb214cfc8bfd0ef3031e2737.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:fba1e4a5d3f30708bb925e0d0b93d420c26b17707f45fceb34e579f5f624c772 +size 10361 diff --git a/data/d2/ord_dataset-d26118acda314269becc35db5c22dc59.parquet b/data/d2/ord_dataset-d26118acda314269becc35db5c22dc59.parquet new file mode 100644 index 0000000000000000000000000000000000000000..1272aa74899cb4828add097c537463dc91ba400e --- /dev/null +++ b/data/d2/ord_dataset-d26118acda314269becc35db5c22dc59.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:0a600968a24eff0a440e30685b2cb7b62030693605574105eb57b7f07329700b +size 130893 diff --git a/data/d3/ord_dataset-d319c2a22ecf4ce59db1a18ae71d529c.parquet b/data/d3/ord_dataset-d319c2a22ecf4ce59db1a18ae71d529c.parquet new file mode 100644 index 0000000000000000000000000000000000000000..ed32d280b6151f23ff1daef87dff464fb8fb1bc6 --- /dev/null +++ b/data/d3/ord_dataset-d319c2a22ecf4ce59db1a18ae71d529c.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:d8f8b29f790e168b7f44dcbdd2ca88829bdaea6be54a31369fd964cf9c01da82 +size 30188 diff --git a/data/d9/ord_dataset-d92976309c3a48a3a64a4cf5e7048086.parquet b/data/d9/ord_dataset-d92976309c3a48a3a64a4cf5e7048086.parquet new file mode 100644 index 0000000000000000000000000000000000000000..aaf2bb3b6991d5d9db8c4e851408ac0cac133c9b --- /dev/null +++ b/data/d9/ord_dataset-d92976309c3a48a3a64a4cf5e7048086.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:78c17145099d29458960ffcb6cec7a8987efeae06b100004be2255ff28e54994 +size 3784674 diff --git a/data/dc/ord_dataset-dc0249930af34d17a3c76881a762aebf.parquet b/data/dc/ord_dataset-dc0249930af34d17a3c76881a762aebf.parquet new file mode 100644 index 0000000000000000000000000000000000000000..08b20c0b249a7702c895cca21c5b2ce43d9ed8ff --- /dev/null +++ b/data/dc/ord_dataset-dc0249930af34d17a3c76881a762aebf.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:baaa0748a4a561705df275c3152a67ef52605a33249f674129f24c1abecfb2b9 +size 20160 diff --git a/data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet b/data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet new file mode 100644 index 0000000000000000000000000000000000000000..9bb5994af7b1c4dc7c0e900eb0e78a09f2a957ba --- /dev/null +++ b/data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:428d777066426504896fc2a0352838caba173518056ce83b387d9701f67af08e +size 104636029 diff --git a/data/ee/ord_dataset-eeba974d3c284aed86d1c1d442260a1e.parquet b/data/ee/ord_dataset-eeba974d3c284aed86d1c1d442260a1e.parquet new file mode 100644 index 0000000000000000000000000000000000000000..dd3c4d62d03af0d5d9874584f96e2b865204d7f8 --- /dev/null +++ b/data/ee/ord_dataset-eeba974d3c284aed86d1c1d442260a1e.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:dbf6dae9521463c542fa8abccd2a078742c8052c0af11db842d200d94403fac6 +size 36161 diff --git a/data/fc/ord_dataset-fc83743b978f4deea7d6856deacbfe53.parquet b/data/fc/ord_dataset-fc83743b978f4deea7d6856deacbfe53.parquet new file mode 100644 index 0000000000000000000000000000000000000000..22223a7a7fdf9bdf45dd83d20e9762c502e213b3 --- /dev/null +++ b/data/fc/ord_dataset-fc83743b978f4deea7d6856deacbfe53.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:14095b49acb35adf50d1ff065d7b9d2ccf01d37f57ccaebbb6ce8eddfd11f484 +size 12354 diff --git a/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet b/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet new file mode 100644 index 0000000000000000000000000000000000000000..fde5488e85231ba08b3f902b2407a02e2fa7d6b3 --- /dev/null +++ b/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3 +size 37643 diff --git a/retired_datasets.csv b/retired_datasets.csv new file mode 100644 index 0000000000000000000000000000000000000000..0617a093a666025b4bb35136be7019b341a52bb6 --- /dev/null +++ b/retired_datasets.csv @@ -0,0 +1,500 @@ +retired_dataset_id,retired_name,replacement_dataset_id,replacement_name,replacement_path +ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad,uspto-grants-1976_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a0bc986c3cf848c2a1ea93b297d1ad89,uspto-grants-1976_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-15ce1bcfb62046d9bec87d32620888d5,uspto-grants-1976_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a5669edbeffe43bf8514c1bfede8f882,uspto-grants-1976_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-653be8036d754ce7b8a1c4cd419eaf55,uspto-grants-1976_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761,uspto-grants-1976_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-53cd7fd33c6f4f1c804e187bec94be57,uspto-grants-1976_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7c810806c4564bada4a9550135bbb06f,uspto-grants-1976_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a0071d97083e4e69ae8872417ed2776b,uspto-grants-1976_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7f88a5da29d74264aae5239be74b3981,uspto-grants-1976_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b971427c0b944c56b63bb2356fa8ca69,uspto-grants-1976_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d625331704b34593871e69cd09a5cd83,uspto-grants-1976_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8ca24382d55b4303bc34393399f4110e,uspto-grants-1977_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2a1960001e7d4e89987253631df1362a,uspto-grants-1977_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-39f318aa6ec5450182abaf3662294306,uspto-grants-1977_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-19b9e29d593f4660ab77c07b459da9bb,uspto-grants-1977_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb,uspto-grants-1977_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3,uspto-grants-1977_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-14866e68bb5b47f5929457eecb4eb3a5,uspto-grants-1977_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2cb52357eb5f43c2be56ad5c0662f18f,uspto-grants-1977_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-dc78376bd0a946d1a5a41eec30282b7d,uspto-grants-1977_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-56c07ce5503b46d1805bdf471f8f1c55,uspto-grants-1977_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8f61d01cf5b34e85a3ccc89f8901797b,uspto-grants-1977_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2e96d163c3f64eb5b470e1ea1a41922a,uspto-grants-1977_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c8db783fb93842e89cdcd41afa59a141,uspto-grants-1978_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a,uspto-grants-1978_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b0ddd49dad024fc7a23ae6f474f9c52f,uspto-grants-1978_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-de10a15943a54ac7a3c3e1c774d21392,uspto-grants-1978_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2345345e84034af393f969fc5e7741b6,uspto-grants-1978_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-48929f64ce614f1181a555eafd7c97a6,uspto-grants-1978_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4c8627b52d564809adb9b494879c07c0,uspto-grants-1978_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f,uspto-grants-1978_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-becaf7dc22c44672b22e4b94335cbf08,uspto-grants-1978_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6d529f04a1724b5d85dcc290cf4c38bb,uspto-grants-1978_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b43eb0158fd54801957aaa07bbdf3057,uspto-grants-1978_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c,uspto-grants-1978_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e5870fef54544989915ccced8dd8d849,uspto-grants-1979_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8881493772e04c4b9495fc2114379967,uspto-grants-1979_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3d470a6df4a04b1996e024a38c53e818,uspto-grants-1979_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-053897d9b1744303b2fdfe3e796ca27b,uspto-grants-1979_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-159c363342e44b539e7a5975c873e30d,uspto-grants-1979_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-12a0ec4f3cda46e2badc694da2072c39,uspto-grants-1979_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-56a7c92b497c48c59951f153285b4adc,uspto-grants-1979_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1590b34936164499aa4ed4fe0ef21255,uspto-grants-1979_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cb9f452f8418479ab5fd99c835dbe015,uspto-grants-1979_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-28b19b59e93c47698a5a2b21048ec201,uspto-grants-1979_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-09e9a37ee5794dc28c0ad7bf7a442c18,uspto-grants-1979_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-912d62c1690b4ebfbe998c0c9baf88a8,uspto-grants-1979_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d9fb402fe3e745c1893a29161cc5dda2,uspto-grants-1980_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9240b22758dd4f9e981f9ad2d5394155,uspto-grants-1980_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b1bf0950b5cb430abbb1d80744f5df84,uspto-grants-1980_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d986d6c6630b41ee8d401fd85be47701,uspto-grants-1980_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8af141577c90485cb9c91079a5ef96b3,uspto-grants-1980_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b5f1497361c94e5fa55257200189a6a4,uspto-grants-1980_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-dabcd66611f34094b1baca0095305a66,uspto-grants-1980_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cb0fdfa937234c78b020ec878a93b94c,uspto-grants-1980_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-06d4002fc4d34860a0688cba690e12dc,uspto-grants-1980_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-520610070b3c4780a03b44c7fcecc28f,uspto-grants-1980_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-10f2568b472a4cabb35c3f313a159005,uspto-grants-1980_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d,uspto-grants-1980_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8868acadaee548d5802e504148fc3b63,uspto-grants-1981_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8c94910e81cc4281bd57a58ce657576f,uspto-grants-1981_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0c37e633e9814a6e886187796cacf216,uspto-grants-1981_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2d589ad46f82417ab9ddc07f7655411c,uspto-grants-1981_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f196f0a87dd74fcd82ca019f8ff5cf9c,uspto-grants-1981_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b1023e5ccd7142de9d250aa2e3e124db,uspto-grants-1981_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7bed824f566d4af0b51d74d386b14bd6,uspto-grants-1981_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-50c29bf1847c44f4b40bfab5f46fe5fe,uspto-grants-1981_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a0b0a122a04c40798e0535b968adcf6e,uspto-grants-1981_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4a4f564f09ba483589e09e154ad32acf,uspto-grants-1981_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6dbd68e494f94ae796187f53698183da,uspto-grants-1981_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-aeb5378e6e67443e8a4f5c7a5ec3de51,uspto-grants-1981_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6ba93916f2ad4247804469d8c2600b26,uspto-grants-1982_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-90c12c4a89ae46d88aea27f4e37ba124,uspto-grants-1982_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-dba7c8cf38834984ba5e6376158f46fe,uspto-grants-1982_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2,uspto-grants-1982_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-62e11cab5a6e47d89878616c244e20ef,uspto-grants-1982_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6f715747ea754945a2f0af4a8482c7d2,uspto-grants-1982_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-be22f1f5114b4ebfb8d447c93d62d62c,uspto-grants-1982_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0bf72e95d80743729fdbb8b57a4bc0c6,uspto-grants-1982_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b37811c5ed724c3b844cc4d2b5640398,uspto-grants-1982_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-10360c60962940178e4bf05e54b1655c,uspto-grants-1982_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e984b2d4813f44d59867e1771acc9b66,uspto-grants-1982_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d06b137b66b3478fb6a0d41a5efd32f8,uspto-grants-1982_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-72d9f7ef86df410fac4765c9632d459b,uspto-grants-1983_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bdb961f26fac426eaa2de8f54a284acf,uspto-grants-1983_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1c61a371eaf841328cc190a0356d6b3b,uspto-grants-1983_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b2a00a09c8494aaf9348c3a3af29d26e,uspto-grants-1983_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45,uspto-grants-1983_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e7e9fe3dd42b4f499d5b17fe63bbf336,uspto-grants-1983_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-64bb36b111c249e0afcce8c5ad9cdbd0,uspto-grants-1983_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-29d79fca4cec4a43b773d0ba25b27651,uspto-grants-1983_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d9235b0d1f9f4e85b2690ee8f860dc30,uspto-grants-1983_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-406d20cb3f314e2c967b14f55925f895,uspto-grants-1983_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21,uspto-grants-1983_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07,uspto-grants-1983_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f3b9c7d90d3648ff8136643f634ef2f0,uspto-grants-1984_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-87aeeef7c91d4312a992c5cea936705c,uspto-grants-1984_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d182ca8cf3f34de69c7a38343db8c930,uspto-grants-1984_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-19041548671f410397ce7f00536a9be3,uspto-grants-1984_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1,uspto-grants-1984_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7a32ed4947a84db9890d8863ca9e55fb,uspto-grants-1984_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9625b7c45a574cd58946dd2c1803eb6f,uspto-grants-1984_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1d493fcbd5494078b46e816998dcb991,uspto-grants-1984_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fea3ada7aaad45a0b4e7922640986af3,uspto-grants-1984_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2,uspto-grants-1984_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d6752864fa634eb3b05f7440b4fb9a70,uspto-grants-1984_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6d96290c60d941d098c4ddc9d0cb01a0,uspto-grants-1984_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833,uspto-grants-1985_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3e4cbfe3ea40460399482e6cf2f9c894,uspto-grants-1985_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e61c1950b2fc468dbf0701c65768f73f,uspto-grants-1985_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d6b60b593b1c4668bc6843cd65a5d232,uspto-grants-1985_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2f37329a4b254471a74f2eb0981f11ec,uspto-grants-1985_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7724d657b6fc42848b62ca7c93d84bed,uspto-grants-1985_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-232d09663ed349c2a1fb1f05d411eae0,uspto-grants-1985_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3,uspto-grants-1985_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b76b52f4448a4eedb28ffcd8f902046a,uspto-grants-1985_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3007013966624a1096d71142f31cb5a3,uspto-grants-1985_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a1d4c9f5edd844798727d514977ca73e,uspto-grants-1985_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884,uspto-grants-1985_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7d359d96b3a64882921ebdc6c850e22e,uspto-grants-1986_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506,uspto-grants-1986_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-343f84c5bd164b25aeae96e1d828e768,uspto-grants-1986_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22,uspto-grants-1986_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1895fe091c3f47afa1ee96a41a250de4,uspto-grants-1986_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d6cdba90760a47779a36ece5962905eb,uspto-grants-1986_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4731a430f0af464b83e8b5b145cd2c77,uspto-grants-1986_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2069a3db775a4d9f9310aca092ecbad8,uspto-grants-1986_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0b70410902ae4139bd5d334881938f69,uspto-grants-1986_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f222e615b1f74f0fabef9cd9b98516b7,uspto-grants-1986_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b9a9e369e9da4413999591aa08f4c3e3,uspto-grants-1986_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-772de90433b44abbbacf9b316b845c31,uspto-grants-1986_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5944a40bb4504bbe8185cfdf2a811d03,uspto-grants-1987_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-128a4f3f44e844218b1c319ab4de3893,uspto-grants-1987_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d1c545e3afc447099315419421478aab,uspto-grants-1987_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-36f7bef430f14c2e8db5e3f7c3640d9b,uspto-grants-1987_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-58ec6779628e43e2b3f0972725f262e6,uspto-grants-1987_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51,uspto-grants-1987_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e402405fd21e4770a14f157cb62ca439,uspto-grants-1987_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c34472859da14a81bfe0f74e60f15c43,uspto-grants-1987_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f5dc3e448c204058b116bf1970695bef,uspto-grants-1987_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1385ebf1988241e49636101695ad79e4,uspto-grants-1987_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-12ef86aced0149e0917be82ce22190e2,uspto-grants-1987_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5c25f386f4664070a72d578feacedf86,uspto-grants-1987_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fdef1f30cad64430bf05cf108d8004a2,uspto-grants-1988_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-01dbb772c5e249108f0b191ed17a2c0c,uspto-grants-1988_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-37d3220f708c49ad839bab296b722248,uspto-grants-1988_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-41558b7e18dd41999311b1762e0e13a3,uspto-grants-1988_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7860c6f563014da8948ede63b7110bde,uspto-grants-1988_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3844acbccc714c04ab757ec4fca10bd0,uspto-grants-1988_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4937da99a6a247eb90fa70f0d2eac3db,uspto-grants-1988_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-07db50a3ce6941919df30a9e2898988f,uspto-grants-1988_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3ef78abb9a384506b240a419b70e6ceb,uspto-grants-1988_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4d84abdf99524e0fb6c42ab2a3300790,uspto-grants-1988_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59,uspto-grants-1988_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2841bde0239a4964a69f490c014a6e43,uspto-grants-1988_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f25e1b7f8ef54305a5170f5395a768c7,uspto-grants-1989_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8537fa92abf34c849134600c0c2bbcc7,uspto-grants-1989_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-754e10d30fb249229e130865010ab25b,uspto-grants-1989_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3ec273742a0345ea916ad5fd071167f2,uspto-grants-1989_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-be83cbc722064f3696975001242f9f1a,uspto-grants-1989_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff,uspto-grants-1989_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0,uspto-grants-1989_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b,uspto-grants-1989_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a58d1baeeea441fb9918c10f18f2cdb9,uspto-grants-1989_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f6fafbb8ce5f4ef099be3a772075ec97,uspto-grants-1989_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-aa9e93ade540499c920a9c3b18e8edaa,uspto-grants-1989_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-31f00a039ca0424788e5e1970d25a8fd,uspto-grants-1989_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-19e5fc80c1554f4f8641c835e055f02b,uspto-grants-1990_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-76a008eb2d3f48d891cad325041f3d1e,uspto-grants-1990_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-72fffaae67c8473fb9d951cb1b026646,uspto-grants-1990_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-dd1de64954674e17b4b690cac09dc67b,uspto-grants-1990_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ac1c7aa04d6c4e588e723e3e05721681,uspto-grants-1990_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e0a818f9350b46cdb184d2ac404ede9f,uspto-grants-1990_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e6e5ffd5405c481d8061087049155f9f,uspto-grants-1990_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b67d30cd146f49dcbf24faee022f1a09,uspto-grants-1990_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2,uspto-grants-1990_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-67ed03c283094854909157b1038e38e3,uspto-grants-1990_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-640d007e35e243a286c8b7dd2b77ac1b,uspto-grants-1990_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6cb04513a4a244c0b612b566096f4b3d,uspto-grants-1990_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-42629b4cf1094978a5e5f29f22639ee7,uspto-grants-1991_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-59f453c3a3d34a89bfd97b6b8b151908,uspto-grants-1991_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1d5bba1436bd42b7a27c43833c25d871,uspto-grants-1991_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-67612e25ea9d4b29966a776893a43d59,uspto-grants-1991_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d98d003e9abb4b579746c5a361466e14,uspto-grants-1991_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac,uspto-grants-1991_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-67c9ee844bf341888b345c8e36183b40,uspto-grants-1991_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11,uspto-grants-1991_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-45d20d09e4d64f45bdd419044025b4d3,uspto-grants-1991_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1acb071a357f438ea5993287375971cf,uspto-grants-1991_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-56e7a343b17a4d6da818127ceb19589d,uspto-grants-1991_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-960c6b9c4fc74afd90a3ebf713215626,uspto-grants-1991_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-685186618e9f4e7aaa72ac40c16ef354,uspto-grants-1992_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9f54014563f44962b72e288618421b97,uspto-grants-1992_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fa3b512e2d924b9b965301ebcba6853d,uspto-grants-1992_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5eb2900a93c842ee98f26c305e657b61,uspto-grants-1992_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1,uspto-grants-1992_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4f3b2ca6df1d41ef8b5008f1f39da0e2,uspto-grants-1992_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-41ea179beba54bed8cd874a5ec3469f7,uspto-grants-1992_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-49bd993346b64eeeb2a8fe2643164a0a,uspto-grants-1992_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cf82113c6dd341d4a014b4667994f01c,uspto-grants-1992_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-30ad5cf6083a45a387b45bebad1a4d65,uspto-grants-1992_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2369b9b9f44641b1930518c59ae89a95,uspto-grants-1992_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b17fdf55f5f945a48d47a588fc255573,uspto-grants-1992_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ab5ba9f863cb41d9924be0bb3c730818,uspto-grants-1993_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c,uspto-grants-1993_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a7bd0db0684c464bb02ff6a36065fee3,uspto-grants-1993_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a2ae447c4340438c8c3a827109aeb425,uspto-grants-1993_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-134cf2fa32ab464880d75db06c38f35a,uspto-grants-1993_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97,uspto-grants-1993_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-347c0709d28a44dea43ca42052be4db3,uspto-grants-1993_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ee287d49cb8642e59ae9c3951f746312,uspto-grants-1993_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-02ee2261663048188cf6d85d2cc96e3f,uspto-grants-1993_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ad17798fcea64e26ba91604fca520090,uspto-grants-1993_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-140fb5527ff24f97bcf0094c5d100120,uspto-grants-1993_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1953a9402dda47b6bcfe3e3cb9ab8a07,uspto-grants-1993_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-769fac6048e548eca2d49e48f972884b,uspto-grants-1994_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d63ab258f4634f87bdebbaff0a341c28,uspto-grants-1994_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc,uspto-grants-1994_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-96711be098434bc9ab567cb77fa3362b,uspto-grants-1994_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5fb693db3950403e9ce1a516570153bf,uspto-grants-1994_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6c3ec086c8c9475e8d31a44641b49e02,uspto-grants-1994_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4,uspto-grants-1994_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bb4579c57ddc48c6a01fad97dacb6293,uspto-grants-1994_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ec7cb3d5a8704f64b01d401ea555974f,uspto-grants-1994_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b6309a86b70f4ca08fd301828cacf950,uspto-grants-1994_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fb70ed83140e4f53a907d87192ad748c,uspto-grants-1994_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9ad0840101374618a7d5c4e4521c82d1,uspto-grants-1994_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9,uspto-grants-1995_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-180e296d6d6245638d4d22a59120ea01,uspto-grants-1995_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a6643d22de674f30a85ba57198b82644,uspto-grants-1995_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-acbdbaa766314b66a982823354e82bf2,uspto-grants-1995_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-081613ef79bd4110aacc146b4465f086,uspto-grants-1995_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-04982f13ed08448d93df6794846500f3,uspto-grants-1995_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-abe42048f0b84fa88446cee56a31e967,uspto-grants-1995_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bd998d3fe946475e835418aaf647c00d,uspto-grants-1995_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fd1553bae35046c7a67523ff472cb5c3,uspto-grants-1995_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430,uspto-grants-1995_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0c61835e3a0b4986aabf2b61b708e322,uspto-grants-1995_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1,uspto-grants-1995_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-24ad29d930104afea313b6c3bd11099e,uspto-grants-1996_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fc4cd2699fc04ecbb7c7c831849e6b22,uspto-grants-1996_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8fe3c7256e6747e59933c880f5f642a0,uspto-grants-1996_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b832171fa1674c469fbd33bc0ca1d5f1,uspto-grants-1996_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2c460e2ef9934444aaf26fec1f75741f,uspto-grants-1996_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1558660634294cc8ad7e01746e9083fd,uspto-grants-1996_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ba1248d90e3e465693710bbc45866f37,uspto-grants-1996_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-65c44df6676d4ce3a1874db5d7958ca9,uspto-grants-1996_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9,uspto-grants-1996_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc,uspto-grants-1996_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d0003732f14e4648a00d341275654590,uspto-grants-1996_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2,uspto-grants-1996_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5,uspto-grants-1997_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-930bf31b476c482e8ba87824089eb600,uspto-grants-1997_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-58ec5adfcd8648dc9e26ee757d289517,uspto-grants-1997_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72,uspto-grants-1997_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742,uspto-grants-1997_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b18df02d6e9345faa0f2dae281a0870a,uspto-grants-1997_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-15cdba4c7f064b3f9cd7343cb3187881,uspto-grants-1997_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ee5599340390470d8e5b5ac1feddf9d6,uspto-grants-1997_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-846d411edee44814931e062174d7ef12,uspto-grants-1997_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-993feac5ecf54388aa6326a220e46db3,uspto-grants-1997_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f367d8d2baac490b9204609a79420961,uspto-grants-1997_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d330662edaed408d950898172aba7a4c,uspto-grants-1997_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-44d518e567bd4c039d77233023f78bb2,uspto-grants-1998_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4bc8addcf9cf4845817557760d62d5b5,uspto-grants-1998_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a,uspto-grants-1998_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a4a191e812a64d0598ea918f047e8da7,uspto-grants-1998_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7fed188163cf4ccca934ec71504c7f8a,uspto-grants-1998_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-55e306db9b6b4befbc22504c12b7113d,uspto-grants-1998_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af,uspto-grants-1998_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2,uspto-grants-1998_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fbdd058349aa456f812e3546c84baab5,uspto-grants-1998_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-275344fd078b4340b89ca0b6e92beb95,uspto-grants-1998_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1cb9d78632144c5f8acfc3e9ff388678,uspto-grants-1998_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-94e21e9990034c729ea727e7d2ab0eb0,uspto-grants-1998_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1a231de00bfe4443b547e1f03885ed41,uspto-grants-1999_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1ecf96d88f254270bff816ee7eeffef6,uspto-grants-1999_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8cce6f317d644b348a7978a2dce3ea01,uspto-grants-1999_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2d21ceeb77844edc9eaedb2fabca2ff1,uspto-grants-1999_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-64e3763e75b242749501bacdc0c8baef,uspto-grants-1999_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9,uspto-grants-1999_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-386da077ab2340638cada986e2ef0770,uspto-grants-1999_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d,uspto-grants-1999_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12,uspto-grants-1999_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ba7561dae3884c07a8beddd0b9f1222e,uspto-grants-1999_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a4f0b79f6b9847168861270b79f84afa,uspto-grants-1999_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3bcdb559226a40d89406474c02d082d1,uspto-grants-1999_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4a5b4fffffb34daa876fff1f127a4135,uspto-grants-2000_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2501595af7f242268dbaab34c9e7ae56,uspto-grants-2000_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1,uspto-grants-2000_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e,uspto-grants-2000_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6c36eb0f817d4144988b8963c5d58879,uspto-grants-2000_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8cd3720738054d76b936f66e14d8cba6,uspto-grants-2000_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb,uspto-grants-2000_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cd531114850e4f239b2a3661044ae672,uspto-grants-2000_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d56f0a7ec215495c92e641d9fa932d28,uspto-grants-2000_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52,uspto-grants-2000_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cb5c1a9eddff4790b1bd650617c32d34,uspto-grants-2000_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7b02d32cc502407f94aea8e5caf405a2,uspto-grants-2000_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-37b0416f244344a08cf357e851eedf2a,uspto-grants-2001_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3f9174c7efcb4f31becbd3516cde9572,uspto-grants-2001_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3,uspto-grants-2001_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8,uspto-grants-2001_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d673d02cdac14dba9ff59f12845a4f37,uspto-grants-2001_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-631d58dab387485c8eb0db4c20a232b7,uspto-grants-2001_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-85c00026681b46f89ef8634d2b8618c3,uspto-grants-2001_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-41760195182e4bb4bc779bd722456071,uspto-grants-2001_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a495451286334c5c9bbcbd48a00c1350,uspto-grants-2001_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-262b40ea420c471da9b9244fe9b8f645,uspto-grants-2001_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-293186f5c9b441cab57f03cd3a18ac26,uspto-grants-2001_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f027aa93238e424fbbf9bad1c7699adc,uspto-grants-2001_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7774db17e619477ea20ee621abe71257,uspto-grants-2002_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b1a34bc8c1204d51a772ed27396c794e,uspto-grants-2002_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27,uspto-grants-2002_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-49124ff635234889bd8dcfe87f4f9013,uspto-grants-2002_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d31180f42ced44719fd9e72685c798bf,uspto-grants-2002_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e967d076b4894c2c854795f019ed3c39,uspto-grants-2002_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ec9decb576c4424c9685993f6262bd9c,uspto-grants-2002_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f483e698250b4da0a84f425c7bfa965a,uspto-grants-2002_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2,uspto-grants-2002_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01,uspto-grants-2002_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e,uspto-grants-2002_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42,uspto-grants-2002_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a9ba4801408c4b01922886164c10a391,uspto-grants-2003_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-60f3171f0342452f8814e7f294e2be8b,uspto-grants-2003_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6,uspto-grants-2003_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7a74d48eeefd45aba53e7258f3ae067a,uspto-grants-2003_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-278fb6af8a994ac69e4d95e6e6eff756,uspto-grants-2003_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-843ef38b45484f72826f5f39d8a29c4d,uspto-grants-2003_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d,uspto-grants-2003_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-273fda773e864aaf9b71a30a2d9f2162,uspto-grants-2003_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-73916d628db147c89020b3baac642d48,uspto-grants-2003_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5c4ee54447b84205a10f9c0473172972,uspto-grants-2003_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb,uspto-grants-2003_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2952e63264f5422a84e12cca1e0541ee,uspto-grants-2003_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c9f990dde2dc45d0948ecbe037a0d819,uspto-grants-2004_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e44331dc51de453ca14b7032593c1958,uspto-grants-2004_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0a66204fc43e49c2922e6f9107e6b62f,uspto-grants-2004_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-de283386b8034acd99fba96d3c7d3227,uspto-grants-2004_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a192df1b44174b5886ef2005f759d553,uspto-grants-2004_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1c0bae7388cf460091d56129e95b3145,uspto-grants-2004_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f,uspto-grants-2004_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c975a50a7600448fabd558f4a94a3e29,uspto-grants-2004_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5d77a731aa10488794c824ad12021f57,uspto-grants-2004_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-271c0b74f4794a06992957029b3151ba,uspto-grants-2004_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fe016e2f90e741a590ad77fd5933161f,uspto-grants-2004_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f5d908a6dcb44353a706166b5e9f7f88,uspto-grants-2004_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-be508e976bbb4586a0cc3368302a62f8,uspto-grants-2005_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-04d607efe1d9485eb99fafa06880f62e,uspto-grants-2005_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5a3d853c53674888a5691dce2e398792,uspto-grants-2005_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c5ee194443334d3e92aff17e46e33bd1,uspto-grants-2005_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e90cd41afe844e49875435eb99903799,uspto-grants-2005_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-632f0d9054ce41aba87d4970966c34a6,uspto-grants-2005_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-50cdc205280641d2a3e264f32908e3d0,uspto-grants-2005_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a,uspto-grants-2005_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-359b8fc87f4244be89d6f02bc5036eac,uspto-grants-2005_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-56747de2718a4ac5bf061651d1cc9e3e,uspto-grants-2005_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6214af00a7eb47f3887ef21a94320a7e,uspto-grants-2005_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-35824232b132464aa99e71aba765981d,uspto-grants-2005_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a7baa616c65d42559e25ca0ba61e0744,uspto-grants-2006_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4e9c2fa02a7544fd839206719263345f,uspto-grants-2006_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bbd7e53f000345838ad4920a07a169ff,uspto-grants-2006_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c408dfed796e4354b61e312e67f7143f,uspto-grants-2006_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c8069773c1a148aca8ab417108daacc5,uspto-grants-2006_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c8a367b56b4f406b878f51867b157d19,uspto-grants-2006_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa,uspto-grants-2006_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0387783899c642a8b7eb4ba379bcdf5d,uspto-grants-2006_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-eb4226b4f7644a01a737e7547b70014a,uspto-grants-2006_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-76dd1b78ee414d2da0ed30700ef026f7,uspto-grants-2006_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-437aa6654d5044ddaef3346dc4c6e08a,uspto-grants-2006_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4b705442211b4a3988e26d5f65098160,uspto-grants-2006_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-844a22e1fcab44a5b59c5e2922b2855a,uspto-grants-2007_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1b0cd79134f0450eaac8396a4f956c30,uspto-grants-2007_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2e58cb8db2bf482bbea23283b7e04488,uspto-grants-2007_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7a8649d55889427e85b208ae89475895,uspto-grants-2007_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8214eb8444a44dc2900ccb42dbeff15e,uspto-grants-2007_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bf316bf78f4f45d4b275959c08104b7c,uspto-grants-2007_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde,uspto-grants-2007_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4ad5db8537994579bef51f16dd8bf0bd,uspto-grants-2007_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-530502f8e61e455784f93c5faa45c94b,uspto-grants-2007_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-744b04e8228742eb9aa4bde36f5dedf1,uspto-grants-2007_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a2d74266062e4398bc26c4f876903ab8,uspto-grants-2007_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7,uspto-grants-2007_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb,uspto-grants-2008_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b,uspto-grants-2008_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-892acf7477db4d3a8a8559f004a7c0a2,uspto-grants-2008_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-50f99930fc41474db226bc80774b38df,uspto-grants-2008_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ec58fad8331a42c5a67ad75aac6713b4,uspto-grants-2008_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0ca5627a13c049a99463095023b09fe5,uspto-grants-2008_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f,uspto-grants-2008_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ec576c604a9d47258c87c732a043ec71,uspto-grants-2008_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-074f86301ec5441ab3b52d902ac06949,uspto-grants-2008_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e2b35e721c2741999b0005d12691f9fe,uspto-grants-2008_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-171b840ae6e84e45bab43b987d09f5c7,uspto-grants-2008_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-faa0236be76c4501841c954527cd1b6c,uspto-grants-2008_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-93908aaae836460ebd48d733eccad483,uspto-grants-2009_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b8b98725045d45bdbd73512048f4b47e,uspto-grants-2009_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b,uspto-grants-2009_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e1c3af9b105b4af09a5171403bbfc06f,uspto-grants-2009_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3592bd645cd143ee8274cd0d834ae581,uspto-grants-2009_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae,uspto-grants-2009_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-11068b1e475b4c5b82e56726ab0dddb7,uspto-grants-2009_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded,uspto-grants-2009_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4,uspto-grants-2009_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c663259b80f947e2a8923796fb0e9a6b,uspto-grants-2009_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d,uspto-grants-2009_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cc0899cd744f4f7f8e7f2463560faad1,uspto-grants-2009_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6,uspto-grants-2010_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-90b0aa1f83334a02919b2be3a1c04542,uspto-grants-2010_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ed680843f6d14f5c9901869b2a06b4a4,uspto-grants-2010_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8,uspto-grants-2010_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ed65749688da45af8a8432967b017729,uspto-grants-2010_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-03ba810b7f464a06b5d8787af2e8b64e,uspto-grants-2010_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f886e51ba1484c76a94bce1482f1eab9,uspto-grants-2010_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-35b56288528641309a040cc2b6710b61,uspto-grants-2010_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b6d8835b0c934476a36e6149e7597487,uspto-grants-2010_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-70899a0178cc441482746c093624afa0,uspto-grants-2010_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7448b89163bf426c9d9777809ce24cec,uspto-grants-2010_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f024e9664ab64906a71a2ff6004cb3d0,uspto-grants-2010_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-136cfada6ce247b4919085a57363459e,uspto-grants-2011_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-83acb82dc5ba4f7aba439b9875aaac43,uspto-grants-2011_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3af92aec23dc4810b92eb0d8c60023ee,uspto-grants-2011_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-dd320ded4b3f4764af39de99491533f7,uspto-grants-2011_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-373415d3e0e54004837cf4831e67666f,uspto-grants-2011_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-ffbef48837674f39816de887b5dc8bae,uspto-grants-2011_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5df93261afc143c3ae919a57ff4fc1d4,uspto-grants-2011_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-afd812677c134591a99f46ce28de2524,uspto-grants-2011_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-52a37d876ddb453e86de0c15fa233d29,uspto-grants-2011_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-af85e6f81c2d49f08086afd6d9e6959c,uspto-grants-2011_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-375a420ee9b042918ddca20f02df37d3,uspto-grants-2011_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4226e9b4f9f845db967ed997270dcafc,uspto-grants-2011_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-285df12e34cd46e993e3c8ebc3a8962a,uspto-grants-2012_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820,uspto-grants-2012_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-68715347640045adb1b09e6a04722b0e,uspto-grants-2012_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-b195433d5c354ddfb6cde0d53c41910f,uspto-grants-2012_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880,uspto-grants-2012_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0f9d2dbe929a45c3892ae75e81e99443,uspto-grants-2012_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff,uspto-grants-2012_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4e81c470cc3b429faf5e1caa50f70a98,uspto-grants-2012_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fb72428f30234761b4216139dc228d0c,uspto-grants-2012_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777,uspto-grants-2012_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cde802cdb7434a5f82a22981ccaefc4e,uspto-grants-2012_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e96f5a2842f14e5380461c234100f05a,uspto-grants-2012_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c544c0c663f54dbea4ddb52ddde7934e,uspto-grants-2013_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0,uspto-grants-2013_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc,uspto-grants-2013_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d5c54236ecd94d61aaa071461bcfc426,uspto-grants-2013_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c,uspto-grants-2013_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-78c3f723155a4347a902b53bcee1524d,uspto-grants-2013_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-2d6edb8ffd434003bb508360153bd9bb,uspto-grants-2013_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cfad8b3f00044bcda60a96b019f09872,uspto-grants-2013_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-08852243bba44cb28769a5833f1515fe,uspto-grants-2013_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-6034127657614f02860ed057b62b882e,uspto-grants-2013_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d932d1d683704a8bad3d064bcb197acc,uspto-grants-2013_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81,uspto-grants-2013_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-31641fb65b34430fa7435229b949b604,uspto-grants-2014_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-12dc3bd21bcf44d09e5b4249afe15161,uspto-grants-2014_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-7456bda2326f4bebaa874a5474d4cc0d,uspto-grants-2014_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f,uspto-grants-2014_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-5e6956e6e8c24a168866a253f4a66c6c,uspto-grants-2014_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-275a3da8f45f4536ad29727f0ef9ba66,uspto-grants-2014_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-a86112d52cd54525a5e36d41f18aced2,uspto-grants-2014_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-fd1fa959d6264608b0b7fcda16741bfd,uspto-grants-2014_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c3c1091f873b4f40827973a6f1f9b685,uspto-grants-2014_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2,uspto-grants-2014_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-1a1aa5d1c3224edca0aec6e3398da985,uspto-grants-2014_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8c74302143c04eb9983e4b3a7ead2d72,uspto-grants-2014_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-8d5c200bca27407ab9febe7598e16458,uspto-grants-2015_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-cac8df8aff894288876df4e093c9877f,uspto-grants-2015_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-4e54080057a44c3887653391e24c90b6,uspto-grants-2015_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9741bb5fd93044078df2a45f45733054,uspto-grants-2015_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-380e279f82154dba9e08ab51b3bdd08a,uspto-grants-2015_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-e8c6a25568b64529b960953990e6921f,uspto-grants-2015_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9cecb3a8d3b9494191b28dcefea66af2,uspto-grants-2015_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-35c51552812941cda45194a013d34bb9,uspto-grants-2015_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d,uspto-grants-2015_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-bcc0b01d4f58457a8733b10a099f43ba,uspto-grants-2015_10,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0,uspto-grants-2015_11,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9cc455db05a444779921f786a45b21a6,uspto-grants-2015_12,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3953983e052a4076aa7cc0880b79cb8b,uspto-grants-2016_01,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-c1e70ad912eb438f8d34b1dc681f809a,uspto-grants-2016_02,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-54347fcace774f89850681d6dec8009f,uspto-grants-2016_03,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb,uspto-grants-2016_04,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-36057d699ac5449e9c37eb99abf78b03,uspto-grants-2016_05,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-eacfee6d16d8455a93348409f1b37be4,uspto-grants-2016_06,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-60a3e71da3174666a50a61dcfa611a9f,uspto-grants-2016_07,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-97eb2ab57fec4160922caae33b54d956,uspto-grants-2016_08,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8,uspto-grants-2016_09,ord_dataset-1158e351757f315b93cbcbe7bc55f38e,uspto-grants,data/11/ord_dataset-1158e351757f315b93cbcbe7bc55f38e.parquet +ord_dataset-9fc3edef9c184a1ca682846f02268768,Training data from https://doi.org/10.1039/C8SC04228D (1/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-f65ca20d97ea49548e969f0e8a633933,Training data from https://doi.org/10.1039/C8SC04228D (10/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-0c1e1da868cd46c59efce6d5d4bc3d63,Training data from https://doi.org/10.1039/C8SC04228D (2/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-423c10301cff45cb8e2bddea2ea5088c,Training data from https://doi.org/10.1039/C8SC04228D (3/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-e52a0f66fdfa4d2ebbb136996350b697,Training data from https://doi.org/10.1039/C8SC04228D (4/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-76a0b901ffe64a2ea3752c04631e822b,Training data from https://doi.org/10.1039/C8SC04228D (5/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-0d07c40794ad4a1c8bc28cc4f8ac4184,Training data from https://doi.org/10.1039/C8SC04228D (6/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-6d65cff9c5f346249fd732d328fb85b1,Training data from https://doi.org/10.1039/C8SC04228D (7/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-18997de394014754be4e04946012e12b,Training data from https://doi.org/10.1039/C8SC04228D (8/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet +ord_dataset-0ccd6c23c9ef4238854293a8da501bd3,Training data from https://doi.org/10.1039/C8SC04228D (9/10),ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3,Training data from https://doi.org/10.1039/C8SC04228D,data/e7/ord_dataset-e7830cd6b11158b43994ccfb5ee9acb3.parquet