diff --git a/.gitattributes b/.gitattributes
index bed0738c7eeb449bca98b5d2f33c89a1ee56349a..fd4812f9ea1ddf18bf42df1bad3d2f85c5b89625 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -1,60 +1,3 @@
-*.7z filter=lfs diff=lfs merge=lfs -text
-*.arrow filter=lfs diff=lfs merge=lfs -text
-*.avro filter=lfs diff=lfs merge=lfs -text
-*.bin filter=lfs diff=lfs merge=lfs -text
-*.bz2 filter=lfs diff=lfs merge=lfs -text
-*.ckpt filter=lfs diff=lfs merge=lfs -text
-*.ftz filter=lfs diff=lfs merge=lfs -text
-*.gz filter=lfs diff=lfs merge=lfs -text
-*.h5 filter=lfs diff=lfs merge=lfs -text
-*.joblib filter=lfs diff=lfs merge=lfs -text
-*.lfs.* filter=lfs diff=lfs merge=lfs -text
-*.lz4 filter=lfs diff=lfs merge=lfs -text
-*.mds filter=lfs diff=lfs merge=lfs -text
-*.mlmodel filter=lfs diff=lfs merge=lfs -text
-*.model filter=lfs diff=lfs merge=lfs -text
-*.msgpack filter=lfs diff=lfs merge=lfs -text
-*.npy filter=lfs diff=lfs merge=lfs -text
-*.npz filter=lfs diff=lfs merge=lfs -text
-*.onnx filter=lfs diff=lfs merge=lfs -text
-*.ot filter=lfs diff=lfs merge=lfs -text
-*.parquet filter=lfs diff=lfs merge=lfs -text
+ord_data-* filter=lfs diff=lfs merge=lfs -text
 *.pb filter=lfs diff=lfs merge=lfs -text
-*.pickle filter=lfs diff=lfs merge=lfs -text
-*.pkl filter=lfs diff=lfs merge=lfs -text
-*.pt filter=lfs diff=lfs merge=lfs -text
-*.pth filter=lfs diff=lfs merge=lfs -text
-*.rar filter=lfs diff=lfs merge=lfs -text
-*.safetensors filter=lfs diff=lfs merge=lfs -text
-saved_model/**/* filter=lfs diff=lfs merge=lfs -text
-*.tar.* filter=lfs diff=lfs merge=lfs -text
-*.tar filter=lfs diff=lfs merge=lfs -text
-*.tflite filter=lfs diff=lfs merge=lfs -text
-*.tgz filter=lfs diff=lfs merge=lfs -text
-*.wasm filter=lfs diff=lfs merge=lfs -text
-*.xz filter=lfs diff=lfs merge=lfs -text
-*.zip filter=lfs diff=lfs merge=lfs -text
-*.zst filter=lfs diff=lfs merge=lfs -text
-*tfevents* filter=lfs diff=lfs merge=lfs -text
-# Audio files - uncompressed
-*.pcm filter=lfs diff=lfs merge=lfs -text
-*.sam filter=lfs diff=lfs merge=lfs -text
-*.raw filter=lfs diff=lfs merge=lfs -text
-# Audio files - compressed
-*.aac filter=lfs diff=lfs merge=lfs -text
-*.flac filter=lfs diff=lfs merge=lfs -text
-*.mp3 filter=lfs diff=lfs merge=lfs -text
-*.ogg filter=lfs diff=lfs merge=lfs -text
-*.wav filter=lfs diff=lfs merge=lfs -text
-# Image files - uncompressed
-*.bmp filter=lfs diff=lfs merge=lfs -text
-*.gif filter=lfs diff=lfs merge=lfs -text
-*.png filter=lfs diff=lfs merge=lfs -text
-*.tiff filter=lfs diff=lfs merge=lfs -text
-# Image files - compressed
-*.jpg filter=lfs diff=lfs merge=lfs -text
-*.jpeg filter=lfs diff=lfs merge=lfs -text
-*.webp filter=lfs diff=lfs merge=lfs -text
-# Video files - compressed
-*.mp4 filter=lfs diff=lfs merge=lfs -text
-*.webm filter=lfs diff=lfs merge=lfs -text
+*.pb.gz filter=lfs diff=lfs merge=lfs -text
diff --git a/.github/ISSUE_TEMPLATE/bug_report.md b/.github/ISSUE_TEMPLATE/bug_report.md
new file mode 100644
index 0000000000000000000000000000000000000000..d1ba2bc046f57329090278c0dbe615d68e539ab0
--- /dev/null
+++ b/.github/ISSUE_TEMPLATE/bug_report.md
@@ -0,0 +1,32 @@
+---
+name: Bug report
+about: Create a report to help us improve
+title: ''
+labels: bug
+assignees: ''
+
+---
+
+**Describe the bug**
+A clear and concise description of what the bug is.
+
+**To Reproduce**
+Steps to reproduce the behavior:
+1. Go to '...'
+2. Click on '....'
+3. Scroll down to '....'
+4. See error
+
+**Expected behavior**
+A clear and concise description of what you expected to happen.
+
+**Screenshots**
+If applicable, add screenshots to help explain your problem.
+
+**Desktop (please complete the following information):**
+ - OS: [e.g. iOS]
+ - Browser [e.g. chrome, safari]
+ - Version [e.g. 22]
+
+**Additional context**
+Add any other context about the problem here.
diff --git a/.github/ISSUE_TEMPLATE/feature_request.md b/.github/ISSUE_TEMPLATE/feature_request.md
new file mode 100644
index 0000000000000000000000000000000000000000..11fc491ef1dae316f2b06bbb40eaba9c757fdfd1
--- /dev/null
+++ b/.github/ISSUE_TEMPLATE/feature_request.md
@@ -0,0 +1,20 @@
+---
+name: Feature request
+about: Suggest an idea for this project
+title: ''
+labels: enhancement
+assignees: ''
+
+---
+
+**Is your feature request related to a problem? Please describe.**
+A clear and concise description of what the problem is. Ex. I'm always frustrated when [...]
+
+**Describe the solution you'd like**
+A clear and concise description of what you want to happen.
+
+**Describe alternatives you've considered**
+A clear and concise description of any alternative solutions or features you've considered.
+
+**Additional context**
+Add any other context or screenshots about the feature request here.
diff --git a/.github/PULL_REQUEST_TEMPLATE/submission.md b/.github/PULL_REQUEST_TEMPLATE/submission.md
new file mode 100644
index 0000000000000000000000000000000000000000..e57e65ebd3c5344aaa4afbf3a2813e624359453d
--- /dev/null
+++ b/.github/PULL_REQUEST_TEMPLATE/submission.md
@@ -0,0 +1,23 @@
+---
+name: Submission
+about: Submit data to the Open Reaction Database
+title: ''
+labels: ''
+assignees: ''
+
+---
+
+**Describe the submission**
+* High-level description of the data
+* Source information (e.g. DOI)
+* Details on how the dataset was created (e.g. web editor, template enumeration, jupyter, etc.)
+* Details about any issues encoding the data (e.g. missing schema fields, ambiguous data, etc.)
+
+**Attach any supporting files**
+
+(Note: they may need to be attached as one or more .zip files)
+* Reaction template and CSV/Excel for enumerated datasets
+* Jupyter notebooks for programmatically defined datasets
+
+---
+[License](https://github.com/open-reaction-database/ord-data/blob/main/LICENSE) • [Terms of Use](https://github.com/open-reaction-database/ord-data/blob/main/CONTRIBUTING.md#terms-of-use) • [Documentation](https://docs.open-reaction-database.org/en/latest/submissions.html)
diff --git a/.github/workflows/submission.yml b/.github/workflows/submission.yml
new file mode 100644
index 0000000000000000000000000000000000000000..73ab62a8e14b97007a43684894bdda0156002704
--- /dev/null
+++ b/.github/workflows/submission.yml
@@ -0,0 +1,169 @@
+# Runs process_dataset.py on all new and changed files.
+#
+# Submissions from forks only trigger the "validation" step to validate the new
+# data. After merging into a new branch in the parent repo, the workflow will
+# run again and trigger the "update" step to add reaction IDs, etc. in
+# preparation for merging into the "main" branch.
+
+name: Submission
+
+on: [pull_request, push]
+
+env:
+  ORD_SCHEMA_TAG: v0.3.93
+
+jobs:
+  count_reactions:
+    if: >-
+      github.event_name == 'pull_request' &&
+      ! github.event.pull_request.head.repo.fork
+    runs-on: ubuntu-latest
+    steps:
+    - name: Checkout ord-data
+      uses: actions/checkout@v2
+      with:
+        ref: ${{ github.event.pull_request.head.sha }}
+        lfs: true
+      if: github.event_name == 'pull_request'
+    - name: Checkout ord-schema
+      uses: actions/checkout@v2
+      with:
+        repository: Open-Reaction-Database/ord-schema
+        ref: ${{ env.ORD_SCHEMA_TAG }}
+        path: ord-schema
+    - uses: actions/setup-python@v4
+      with:
+        python-version: '3.11'
+    - name: Install ord_schema
+      run: |
+        cd "${GITHUB_WORKSPACE}/ord-schema"
+        python -m pip install --upgrade pip
+        python -m pip install wheel
+        python -m pip install .
+    - name: Update reactions badge
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        python ord-schema/badges/reactions.py --root=data --output=badges/reactions.svg
+        git add badges/reactions.svg
+        git config user.name github-actions
+        git config user.email github-actions@github.com
+        # Fail gracefully if there is nothing to commit.
+        git commit -a -m "Update badges" || (( $? == 1 ))
+        git push "https://${GITHUB_ACTOR}:${GITHUB_TOKEN}@github.com/${GITHUB_REPOSITORY}.git" "HEAD:${GITHUB_HEAD_REF}"
+
+  check_file_types:
+    runs-on: ubuntu-latest
+    steps:
+    - uses: actions/checkout@v2
+    - name: Add upstream for comparisons to HEAD
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        git remote add upstream \
+          "https://github.com/Open-Reaction-Database/${GITHUB_REPOSITORY##*/}.git"
+        echo "Current branch: $(git rev-parse --abbrev-ref HEAD)"
+        git fetch --no-tags --prune --depth=1 upstream \
+          +refs/heads/*:refs/remotes/upstream/*
+    - name: Check changed files (PR from fork)
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        git diff --name-only upstream/main > changed_files.txt
+        grep -vE '\.pb(txt)?(.gz)?$' changed_files.txt && \
+          echo "Error: submissions should only contain (gzipped) *.pbtxt or *.pb files" && \
+          exit 1 || true
+      if: >-
+        github.event_name == 'pull_request' &&
+        github.event.pull_request.head.repo.fork
+
+  check_target_branch:
+    runs-on: ubuntu-latest
+    steps:
+    - name: Check target branch
+      run: |
+        echo "Target branch: ${GITHUB_BASE_REF}"
+        test "${GITHUB_BASE_REF}" != "main"
+      if: >-
+        github.event_name == 'pull_request' &&
+        github.event.pull_request.head.repo.fork
+
+  process_submission:
+    runs-on: ubuntu-latest
+    steps:
+    - name: Checkout ord-data
+      uses: actions/checkout@v2
+      with:
+        lfs: true
+      if: github.event_name == 'push'
+    - name: Checkout ord-data
+      uses: actions/checkout@v2
+      with:
+        ref: ${{ github.event.pull_request.head.sha }}
+        lfs: true
+      if: github.event_name == 'pull_request'
+    - name: Add upstream for comparisons to HEAD
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        git remote add upstream \
+          "https://github.com/Open-Reaction-Database/${GITHUB_REPOSITORY##*/}.git"
+        echo "Current branch: $(git rev-parse --abbrev-ref HEAD)"
+        git fetch --no-tags --prune --depth=1 upstream \
+          +refs/heads/*:refs/remotes/upstream/*
+    - name: Checkout ord-schema
+      uses: actions/checkout@v2
+      with:
+        repository: Open-Reaction-Database/ord-schema
+        ref: ${{ env.ORD_SCHEMA_TAG }}
+        path: ord-schema
+    - name: Identify changed files
+      # NOTE(kearnes): This sets the NUM_CHANGED_FILES variable.
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        git diff --name-status upstream/main > changed_files.txt
+        echo "Found $(wc -l < changed_files.txt | tr -d ' ') changed files"
+        cat changed_files.txt
+        # Use `|| (( $? == 1 ))` in case no lines match (exit code is nonzero).
+        grep -E "\.pb(txt)?(.gz)?$" changed_files.txt > changed_data_files.txt || (( $? == 1 ))
+        # Use LOCAL_NUM_CHANGED since ::set-env values are not available immediately.
+        LOCAL_NUM_CHANGED="$(wc -l < changed_data_files.txt | tr -d ' ')"
+        echo "NUM_CHANGED_FILES=${LOCAL_NUM_CHANGED}" >> $GITHUB_ENV
+        echo "Found ${LOCAL_NUM_CHANGED} changed dataset files"
+        cat changed_data_files.txt
+    - uses: actions/setup-python@v4
+      with:
+        python-version: '3.11'
+      if: env.NUM_CHANGED_FILES != '0'
+    - name: Install ord_schema
+      run: |
+        cd "${GITHUB_WORKSPACE}/ord-schema"
+        python -m pip install --upgrade pip
+        python -m pip install wheel
+        python -m pip install .
+      if: env.NUM_CHANGED_FILES != '0'
+    - name: Validate submission
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        python ./ord-schema/ord_schema/scripts/process_dataset.py \
+          --input_file=changed_data_files.txt \
+          --base=upstream/main
+      if: >-
+        env.NUM_CHANGED_FILES != '0' &&
+        ! (github.event_name == 'pull_request' &&
+           ! github.event.pull_request.head.repo.fork)
+    - name: Update submission
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        python ./ord-schema/ord_schema/scripts/process_dataset.py \
+          --input_file=changed_data_files.txt \
+          --update \
+          --cleanup \
+          --base=upstream/main \
+          --issue=${{ github.event.number }} \
+          --token=${{ secrets.GITHUB_TOKEN }}
+        git config user.name github-actions
+        git config user.email github-actions@github.com
+        # Fail gracefully if there is nothing to commit.
+        git commit -a -m "Update submission" || (( $? == 1 ))
+        git push "https://${GITHUB_ACTOR}:${GITHUB_TOKEN}@github.com/${GITHUB_REPOSITORY}.git" "HEAD:${GITHUB_HEAD_REF}"
+      if: >-
+        env.NUM_CHANGED_FILES != '0' &&
+        github.event_name == 'pull_request' &&
+        ! github.event.pull_request.head.repo.fork
diff --git a/.github/workflows/validation.yml b/.github/workflows/validation.yml
new file mode 100644
index 0000000000000000000000000000000000000000..3513cdfdcc72e8b754fa49c8f48f8224c706996f
--- /dev/null
+++ b/.github/workflows/validation.yml
@@ -0,0 +1,61 @@
+# Runs process_dataset.py on all files in the database.
+
+name: Validation
+
+on:
+  push:
+    branches:
+      - main
+  pull_request:
+    paths:
+      # Runs when this file is modified in a PR.
+      - '.github/workflows/validation.yml'
+
+env:
+  ORD_SCHEMA_TAG: v0.3.93
+
+jobs:
+  validate_database:
+    runs-on: ubuntu-latest
+    strategy:
+      matrix:
+        filter: [
+          'data/[0-4][0-4]',
+          'data/[0-4][5-9]',
+          'data/[0-4][a-f]',
+          'data/[5-9][0-4]',
+          'data/[5-9][5-9]',
+          'data/[5-9][a-f]',
+          'data/[a-f][0-4]',
+          'data/[a-f][5-9]',
+          'data/[a-f][a-f]',
+        ]
+    steps:
+    - name: Checkout ord-data
+      uses: actions/checkout@v2
+      with:
+        lfs: true
+    - name: Checkout ord-schema
+      uses: actions/checkout@v2
+      with:
+        repository: Open-Reaction-Database/ord-schema
+        ref: ${{ env.ORD_SCHEMA_TAG }}
+        path: ord-schema
+    - uses: actions/setup-python@v4
+      with:
+        python-version: '3.11'
+    - name: Install ord_schema
+      run: |
+        cd "${GITHUB_WORKSPACE}/ord-schema"
+        python -m pip install --upgrade pip
+        python -m pip install wheel
+        python -m pip install .
+    - name: Validate datasets
+      env:
+        FILTER: ${{ matrix.filter }}
+      run: |
+        cd "${GITHUB_WORKSPACE}"
+        python ./ord-schema/ord_schema/scripts/validate_dataset.py \
+          --input="data/*/*.pb*" \
+          --filter="${FILTER}" \
+          --n_jobs=4
diff --git a/.gitignore b/.gitignore
new file mode 100644
index 0000000000000000000000000000000000000000..6c2e3e685cca1afff37258d3f7e0a0218616b569
--- /dev/null
+++ b/.gitignore
@@ -0,0 +1,131 @@
+.idea/
+
+# Byte-compiled / optimized / DLL files
+__pycache__/
+*.py[cod]
+*$py.class
+
+# C extensions
+*.so
+
+# Distribution / packaging
+.Python
+build/
+develop-eggs/
+dist/
+downloads/
+eggs/
+.eggs/
+lib/
+lib64/
+parts/
+sdist/
+var/
+wheels/
+pip-wheel-metadata/
+share/python-wheels/
+*.egg-info/
+.installed.cfg
+*.egg
+MANIFEST
+
+# PyInstaller
+#  Usually these files are written by a python script from a template
+#  before PyInstaller builds the exe, so as to inject date/other infos into it.
+*.manifest
+*.spec
+
+# Installer logs
+pip-log.txt
+pip-delete-this-directory.txt
+
+# Unit test / coverage reports
+htmlcov/
+.tox/
+.nox/
+.coverage
+.coverage.*
+.cache
+nosetests.xml
+coverage.xml
+*.cover
+*.py,cover
+.hypothesis/
+.pytest_cache/
+
+# Translations
+*.mo
+*.pot
+
+# Django stuff:
+*.log
+local_settings.py
+db.sqlite3
+db.sqlite3-journal
+
+# Flask stuff:
+instance/
+.webassets-cache
+
+# Scrapy stuff:
+.scrapy
+
+# Sphinx documentation
+docs/_build/
+
+# PyBuilder
+target/
+
+# Jupyter Notebook
+.ipynb_checkpoints
+
+# IPython
+profile_default/
+ipython_config.py
+
+# pyenv
+.python-version
+
+# pipenv
+#   According to pypa/pipenv#598, it is recommended to include Pipfile.lock in version control.
+#   However, in case of collaboration, if having platform-specific dependencies or dependencies
+#   having no cross-platform support, pipenv may install dependencies that don't work, or not
+#   install all needed dependencies.
+#Pipfile.lock
+
+# PEP 582; used by e.g. github.com/David-OConnor/pyflow
+__pypackages__/
+
+# Celery stuff
+celerybeat-schedule
+celerybeat.pid
+
+# SageMath parsed files
+*.sage.py
+
+# Environments
+.env
+.venv
+env/
+venv/
+ENV/
+env.bak/
+venv.bak/
+
+# Spyder project settings
+.spyderproject
+.spyproject
+
+# Rope project settings
+.ropeproject
+
+# mkdocs documentation
+/site
+
+# mypy
+.mypy_cache/
+.dmypy.json
+dmypy.json
+
+# Pyre type checker
+.pyre/
diff --git a/CITATION.cff b/CITATION.cff
new file mode 100644
index 0000000000000000000000000000000000000000..994aacd63d39e0f3c8aa7837072fb525bb2ff3b5
--- /dev/null
+++ b/CITATION.cff
@@ -0,0 +1,12 @@
+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
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
new file mode 100644
index 0000000000000000000000000000000000000000..98a8facdbb7c33faac74648c00ec90e38e16815c
--- /dev/null
+++ b/CONTRIBUTING.md
@@ -0,0 +1,91 @@
+# 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.
+   
+## 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.
+
+<p align="center">Open Reaction Database Project License Agreement</p> 
+
+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
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diff --git a/README.md b/README.md
index 340a31bb5f9b74dc06138cb27c713a0410017851..e157c50cd57b491dbe41a295f8b69dcb8c3c532c 100644
--- a/README.md
+++ b/README.md
@@ -1,3 +1,68 @@
----
-license: cc-by-sa-4.0
----
+# ord-data
+
+![](https://github.com/Open-Reaction-Database/ord-data/workflows/Validation/badge.svg)
+![](https://raw.githubusercontent.com/Open-Reaction-Database/ord-data/main/badges/reactions.svg)
+[![DOI](https://zenodo.org/badge/283813042.svg)](https://zenodo.org/badge/latestdoi/283813042)
+
+## Cloning with Git LFS
+
+We use [Git LFS](https://git-lfs.github.com) to efficiently store
+the Dataset records that make up the ORD. To view these files locally, you'll
+need to install Git LFS before cloning the repository.
+
+## Data Manipulation
+
+The `ord-data` repository contains the Open Reaction Database (ORD) in Google's Protobuf binary
+format, which is stored in the [`data`](data) directory. Currently, all the data are stored in e.g.
+*.pb.gz format (compressed Protobuf binary files) for the sake of efficiency. The user can convert
+the data into human readable text format, *.pb.txt.
+
+```python
+# import requirements
+from ord_schema.message_helpers import load_message, write_message
+from ord_schema.proto import dataset_pb2
+
+# load the binary ord file
+dataset = load_message("input_fname.pb.gz", dataset_pb2.Dataset)
+# save the ord file as human readable text
+write_message(dataset, "output_fname.pbtxt")
+```
+
+We can also convert ORD data into JSON format.
+
+```python
+# import requirements
+import json
+
+from ord_schema.message_helpers import load_message, write_message
+from ord_schema.proto import dataset_pb2
+from google.protobuf.json_format import MessageToJson
+
+input_fname = "sample_file.pb.gz"
+dataset = load_message(
+    input_fname,
+    dataset_pb2.Dataset,
+)
+
+# take one reaction message from the dataset for example
+rxn = dataset.reactions[0]
+rxn_json = json.loads(
+    MessageToJson(
+        message=rxn,
+        including_default_value_fields=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}")
+```
+
+## 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).
diff --git a/badges/reactions.svg b/badges/reactions.svg
new file mode 100644
index 0000000000000000000000000000000000000000..2051ac489546a5d29e11a85bb0b06ba6f68e2365
--- /dev/null
+++ b/badges/reactions.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="122" height="20" role="img" aria-label="Reactions: 2376120"><title>Reactions: 2376120</title><linearGradient id="s" x2="0" y2="100%"><stop offset="0" stop-color="#bbb" stop-opacity=".1"/><stop offset="1" stop-opacity=".1"/></linearGradient><clipPath id="r"><rect width="122" height="20" rx="3" fill="#fff"/></clipPath><g clip-path="url(#r)"><rect width="63" height="20" fill="#555"/><rect x="63" width="59" height="20" fill="#007ec6"/><rect width="122" height="20" fill="url(#s)"/></g><g fill="#fff" text-anchor="middle" font-family="Verdana,Geneva,DejaVu Sans,sans-serif" text-rendering="geometricPrecision" font-size="110"><text aria-hidden="true" x="325" y="150" fill="#010101" fill-opacity=".3" transform="scale(.1)" textLength="530">Reactions</text><text x="325" y="140" transform="scale(.1)" fill="#fff" textLength="530">Reactions</text><text aria-hidden="true" x="915" y="150" fill="#010101" fill-opacity=".3" transform="scale(.1)" textLength="490">2376120</text><text x="915" y="140" transform="scale(.1)" fill="#fff" textLength="490">2376120</text></g></svg>
\ No newline at end of file
diff --git a/data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.pb.gz b/data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.pb.gz
new file mode 100644
index 0000000000000000000000000000000000000000..5e206e74ff4ca40078e934e4d95cf8cd91d5e61c
--- /dev/null
+++ b/data/00/ord_dataset-00005539a1e04c809a9a78647bea649c.pb.gz
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:491531891f31ad2bbfdfccf347e265fa82b7e2bd7fda5813d6473dd309c29d4a
+size 261136
diff --git a/data/01/ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a.pb.gz b/data/01/ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a.pb.gz
new file mode 100644
index 0000000000000000000000000000000000000000..5009409a66679740355662bd69656427d3e90128
--- /dev/null
+++ b/data/01/ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a.pb.gz
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:1a8b011c47a40c583ed9f56bc1bd95f72e2b0d7f0e65e16c144e344b199e29ac
+size 1788733
diff --git a/data/01/ord_dataset-01dbb772c5e249108f0b191ed17a2c0c.pb.gz b/data/01/ord_dataset-01dbb772c5e249108f0b191ed17a2c0c.pb.gz
new file mode 100644
index 0000000000000000000000000000000000000000..1febf927779cbcec63f8dd6f4bf059d3734fe2ab
--- /dev/null
+++ b/data/01/ord_dataset-01dbb772c5e249108f0b191ed17a2c0c.pb.gz
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:37197d7ebd29eeeab32ae5439a581a1ca65ec94064ae5966a5d4c2d327ffccbc
+size 683353
diff --git a/data/02/ord_dataset-02ee2261663048188cf6d85d2cc96e3f.pb.gz b/data/02/ord_dataset-02ee2261663048188cf6d85d2cc96e3f.pb.gz
new file mode 100644
index 0000000000000000000000000000000000000000..e8cda47178710bb214443a076e6aa6e6d04e7c92
--- /dev/null
+++ b/data/02/ord_dataset-02ee2261663048188cf6d85d2cc96e3f.pb.gz
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+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"
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+    key: "Amine"
+    value {
+      components {
+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
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+            units: MICROMOLE
+          }
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+        identifiers {
+          type: SMILES
+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
+        }
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+          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 {
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+            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 {
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
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+    value {
+      components {
+        identifiers {
+          type: SMILES
+          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
+        }
+        amount {
+          moles {
+            value: 0.5
+            units: MICROMOLE
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+        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
+      }
+    }
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+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+    temperature {
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+        type: DRY_ALUMINUM_PLATE
+      }
+      setpoint {
+        value: 80.0
+        units: CELSIUS
+      }
+    }
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+      details: "Magnetic Stir Bar"
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+    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"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+        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 {
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
+        }
+        amount {
+          volume {
+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
+  }
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+      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 {
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+        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"
+}
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+  inputs {
+    key: "Amine"
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+      components {
+        identifiers {
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+          value: "C1CCNCC1"
+        }
+        amount {
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+            value: 3.75
+            units: MICROMOLE
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+      }
+      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
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+        identifiers {
+          type: SMILES
+          value: "CS(=O)C"
+        }
+        amount {
+          volume {
+            value: 12.5
+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
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+          value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br"
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+            units: MICROMOLE
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+          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
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+          value: "CS(=O)C"
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
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+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+      }
+      setpoint {
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
+    }
+  }
+  workups {
+    type: ADDITION
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+      components {
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+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
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+            units: MICROLITER
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+          value: "CC(=O)O"
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+            units: MICROLITER
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            units: MICROMOLE
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+    amount {
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+        value: 25.0
+        units: MICROLITER
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+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
+        }
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+            units: MICROLITER
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+        }
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+      units: HOUR
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+        value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4"
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
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+        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)"
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+      }
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+    experimenter {
+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      time {
+        value: "6/2/2021, 8:10:58 AM"
+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
+    }
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+}
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+  inputs {
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+          value: "C1CCNCC1"
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+        }
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+        is_limiting: false
+      }
+      components {
+        identifiers {
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+          }
+        }
+        reaction_role: REAGENT
+      }
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+          value: "[Cu]I"
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+          type: SMILES
+          value: "CS(=O)C"
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+            units: MICROLITER
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+    }
+  }
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+          value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C"
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+            units: MICROMOLE
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+      }
+      addition_order: 1
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+          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
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+        units: CELSIUS
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+        units: MICROLITER
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+      reaction_role: PRODUCT
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+      time {
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
+    }
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+      time {
+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+      details: "Automatic updates from the submission pipeline."
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+}
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+        units: MICROLITER
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+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
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+      }
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+      details: "Automatic updates from the submission pipeline."
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+}
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+    }
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+        type: GLASS
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+        value: 250.0
+        units: MICROLITER
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+      details: "Nitrogen Filled"
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+        type: DRY_ALUMINUM_PLATE
+      }
+      setpoint {
+        value: 80.0
+        units: CELSIUS
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+            units: MICROLITER
+          }
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+        value: 25.0
+        units: MICROLITER
+      }
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+    type: ADDITION
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
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+            units: MICROLITER
+          }
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+        reaction_role: WORKUP
+      }
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+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
+      value {
+        type: LCMS
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+        instrument_manufacturer: "Waters"
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+    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"
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+      time {
+        value: "6/2/2021, 8:10:58 AM"
+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
+    }
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+      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."
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+}
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+        units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+      reaction_role: PRODUCT
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+      value {
+        type: LCMS
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+        instrument_manufacturer: "Waters"
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+    }
+  }
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+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    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."
+    }
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+}
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+        units: MICROLITER
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+          type: SMILES
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+        }
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+      reaction_role: PRODUCT
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+        instrument_manufacturer: "Waters"
+      }
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
+    }
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+        units: CELSIUS
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+      reaction_role: PRODUCT
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+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    city: "Rahway, NJ"
+    doi: "10.1039/C5SC04751J"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+}
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+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+        units: CELSIUS
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+      reaction_role: PRODUCT
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      time {
+        value: "6/2/2021, 8:10:58 AM"
+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
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+      time {
+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+}
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
+    }
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+        orcid: "0000-0001-6735-4696"
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+      }
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
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+}
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+      details: "Automatic updates from the submission pipeline."
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+}
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+      email: "spencer_dreher@merck.com"
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+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
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+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+      email: "spencer_dreher@merck.com"
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+      }
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+      details: "Automatic updates from the submission pipeline."
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+}
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+      reaction_role: PRODUCT
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+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
+    }
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      time {
+        value: "6/2/2021, 8:10:58 AM"
+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
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+      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."
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+}
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+      email: "spencer_dreher@merck.com"
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
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+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
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+      details: "Automatic updates from the submission pipeline."
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+}
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+      }
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+        orcid: "0000-0001-6735-4696"
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+        units: CELSIUS
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+      }
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+          type: SMILES
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+        units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
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+        }
+        reaction_role: WORKUP
+      }
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+      units: HOUR
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+        type: SMILES
+        value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C"
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
+          value: 78.0
+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      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."
+    }
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+}
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+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+          type: SMILES
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+      }
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+        uses_internal_standard: true
+        is_normalized: true
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+      reaction_role: PRODUCT
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+      key: "UPLC-MS"
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+      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"
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+        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."
+    }
+  }
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+}
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+        units: MICROLITER
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+        units: MICROLITER
+      }
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+        uses_authentic_standard: false
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+      reaction_role: PRODUCT
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
+    }
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      time {
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+      }
+      person {
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+        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."
+    }
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+}
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+          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
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+      }
+      addition_order: 1
+    }
+  }
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+        units: MICROLITER
+      }
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+      details: "Nitrogen Filled"
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+    temperature {
+      control {
+        type: DRY_ALUMINUM_PLATE
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+        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."
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+      components {
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+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
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+        }
+        reaction_role: WORKUP
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+        units: MICROLITER
+      }
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+    type: ADDITION
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+          volume {
+            value: 700.0
+            units: MICROLITER
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+        }
+        reaction_role: WORKUP
+      }
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+      units: HOUR
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+        type: SMILES
+        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
+          value: 50.56
+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      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"
+      }
+    }
+  }
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+    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."
+    }
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+}
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+        units: CELSIUS
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+        units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
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+      value {
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+        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)"
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+      }
+    }
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    city: "Rahway, NJ"
+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
+    record_created {
+      time {
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+      }
+      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."
+    }
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+}
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+        units: MICROLITER
+      }
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+        is_normalized: true
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+        }
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+      reaction_role: PRODUCT
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+      }
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      }
+      person {
+        name: "Michael Wleklinski"
+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
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+      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."
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+}
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+      }
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+    }
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+      details: "Nitrogen Filled"
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+        type: DRY_ALUMINUM_PLATE
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+        units: CELSIUS
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+    }
+    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."
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            value: 5.0
+            units: MICROLITER
+          }
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+          value: "1,3,5-trimethoxybenzene"
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+        units: MICROLITER
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+          details: "NAME resolved by the PubChem API"
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+        }
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+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
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+        type: SMILES
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+        uses_authentic_standard: false
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
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+      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."
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+}
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+        units: MICROLITER
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+        is_normalized: true
+        uses_authentic_standard: false
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+        }
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+      reaction_role: PRODUCT
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
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+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
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+    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."
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+}
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+        units: MICROLITER
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+    }
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+      }
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+      setpoint {
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
+    }
+  }
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+    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."
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+          details: "NAME resolved by the PubChem API"
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+        }
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+    type: ALIQUOT
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+        value: 25.0
+        units: MICROLITER
+      }
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+    type: ADDITION
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+          type: SMILES
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+          value: "CC#N"
+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
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+        }
+        reaction_role: WORKUP
+      }
+    }
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+        type: SMILES
+        value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO"
+      }
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+        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."
+    }
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+}
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+        units: MICROLITER
+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      units: HOUR
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+      measurements {
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+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
+      value {
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+        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"
+}
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+            units: MICROMOLE
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+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
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+        units: MICROLITER
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+        units: CELSIUS
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+            units: MICROMOLE
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+        units: MICROLITER
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+        }
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+        instrument_manufacturer: "Waters"
+      }
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+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
+    }
+    city: "Rahway, NJ"
+    doi: "10.1039/C5SC04751J"
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+    record_created {
+      time {
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+      }
+      person {
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+        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."
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+  }
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+}
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
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+      }
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+  inputs {
+    key: "Catalyst"
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+      components {
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+  }
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+      details: "96 Glass Vials"
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+      }
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+      details: "Nitrogen Filled"
+    }
+  }
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+        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."
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
+        }
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+            units: MICROLITER
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+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
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+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROMOLE
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+      }
+    }
+  }
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+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
+    amount {
+      volume {
+        value: 25.0
+        units: MICROLITER
+      }
+    }
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+      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."
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+}
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+        is_normalized: true
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
+    }
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
+    }
+  }
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+}
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+        units: CELSIUS
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+      organization: "Merck"
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+      }
+      person {
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
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+        value: "Wed Jul  7 21:27:17 2021"
+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+    }
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+        type: DRY_ALUMINUM_PLATE
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
+  }
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+    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."
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+        units: MICROLITER
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+  }
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+    input {
+      components {
+        identifiers {
+          type: SMILES
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+          value: "CC#N"
+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
+  }
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+    reaction_time {
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+      units: HOUR
+    }
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+      identifiers {
+        type: SMILES
+        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
+      }
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+        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."
+    }
+  }
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+}
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+  inputs {
+    key: "Amine"
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+            units: MICROLITER
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+        units: MICROLITER
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+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+        units: CELSIUS
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+        units: MICROLITER
+      }
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+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
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+            units: MICROLITER
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+      units: HOUR
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+        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
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+        instrument_manufacturer: "Waters"
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+    }
+  }
+  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."
+    }
+  }
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+}
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+      }
+      addition_order: 2
+    }
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+            units: MICROMOLE
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+        units: MICROLITER
+      }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
+    }
+    analyses {
+      key: "UPLC-MS"
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+        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"
+      }
+    }
+  }
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+    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 {
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+        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."
+    }
+  }
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+}
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+        }
+        reaction_role: SOLVENT
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+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
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+    value {
+      components {
+        identifiers {
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+      }
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+    }
+  }
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+      details: "96 Glass Vials"
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+        units: MICROLITER
+      }
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+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
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+      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"
+        }
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+            units: MICROLITER
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+          value: "CC(=O)O"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROMOLE
+          }
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+        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"
+        }
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+            units: MICROLITER
+          }
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+      }
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+        }
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
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+        instrument_manufacturer: "Waters"
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+    }
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+    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."
+    }
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+}
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      }
+      person {
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+        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."
+    }
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+}
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+        units: MICROLITER
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
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+        orcid: "0000-0001-6735-4696"
+        organization: "Merck"
+        email: "michael.wleklinski@merck.com"
+      }
+    }
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+      }
+      person {
+        username: "github-actions"
+        email: "github-actions@github.com"
+      }
+      details: "Automatic updates from the submission pipeline."
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+}
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+      }
+      addition_order: 1
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+        units: MICROLITER
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+      setpoint {
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+        units: CELSIUS
+      }
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+      details: "Magnetic Stir Bar"
+    }
+  }
+  workups {
+    type: ADDITION
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+          details: "NAME resolved by the PubChem API"
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+        identifiers {
+          type: SMILES
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+    }
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+        value: 25.0
+        units: MICROLITER
+      }
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+    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"
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+        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"
+}
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+  inputs {
+    key: "Amine"
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          value: "[Cu]I"
+        }
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+            units: MICROMOLE
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+            units: MICROLITER
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+          volume_includes_solutes: true
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+          value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl"
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+        type: DRY_ALUMINUM_PLATE
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
+        }
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+            units: MICROLITER
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+        }
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+            value: 5.0
+            units: MICROLITER
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+            units: MICROMOLE
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+        }
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+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
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+        value: 25.0
+        units: MICROLITER
+      }
+    }
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+    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"
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+            value: 700.0
+            units: MICROLITER
+          }
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+        reaction_role: WORKUP
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+      value: 18.0
+      units: HOUR
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+        type: SMILES
+        value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl"
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+      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
+    }
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+      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"
+}
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+        }
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+            units: MICROMOLE
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+            units: MICROMOLE
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+        }
+        reaction_role: REAGENT
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+          value: "[Cu]I"
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+            units: MICROMOLE
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+            units: MICROLITER
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+        identifiers {
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+          value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br"
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+            units: MICROMOLE
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+        }
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+        is_limiting: true
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+        units: MICROLITER
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+        units: CELSIUS
+      }
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+      details: "Magnetic Stir Bar"
+    }
+  }
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+    type: ADDITION
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+          details: "NAME resolved by the PubChem API"
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+        }
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+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROMOLE
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+        units: MICROLITER
+      }
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+  }
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+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROLITER
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+      }
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+      units: HOUR
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+        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
+      }
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+        type: YIELD
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+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
+          value: 43.36
+        }
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+      reaction_role: PRODUCT
+    }
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+        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 {
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+      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"
+}
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+        is_limiting: false
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+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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+          value: "[Cu]I"
+        }
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+          value: "CS(=O)C"
+        }
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+            value: 12.5
+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+    key: "Aryl Halide"
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+      components {
+        identifiers {
+          type: SMILES
+          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
+        }
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+            value: 2.5
+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
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+    value {
+      components {
+        identifiers {
+          type: SMILES
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+            units: MICROMOLE
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+          value: "CS(=O)C"
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+            units: MICROLITER
+          }
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 3
+    }
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+      details: "96 Glass Vials"
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+        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 {
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+            units: MICROLITER
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+        }
+        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"
+        }
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+            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"
+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
+  }
+  outcomes {
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+      units: HOUR
+    }
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+        type: SMILES
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+      }
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+        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 {
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          value: "[Cu]I"
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+            units: MICROLITER
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+        units: MICROLITER
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+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+            units: MICROLITER
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+            units: MICROMOLE
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+        reaction_role: INTERNAL_STANDARD
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+    details: "25 microliter of resulting solution is taken"
+    amount {
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+        value: 25.0
+        units: MICROLITER
+      }
+    }
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+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
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+            units: MICROLITER
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+        reaction_role: WORKUP
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+      value: 18.0
+      units: HOUR
+    }
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+        type: SMILES
+        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
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+      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
+    }
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+      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"
+}
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+            units: MICROMOLE
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+        }
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+      }
+      addition_order: 2
+    }
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+        is_limiting: true
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+      addition_order: 1
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+  workups {
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+        }
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+            units: MICROMOLE
+          }
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+    }
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+    details: "25 microliter of resulting solution is taken"
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+        value: 25.0
+        units: MICROLITER
+      }
+    }
+  }
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+    input {
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROLITER
+          }
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+      units: HOUR
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+        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
+      }
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      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."
+    }
+  }
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+}
+reactions {
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+        }
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+            units: MICROMOLE
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+        }
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+        reaction_role: REAGENT
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+            units: MICROMOLE
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+          value: "CS(=O)C"
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+    key: "Aryl Halide"
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+        identifiers {
+          type: SMILES
+          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
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+        identifiers {
+          type: SMILES
+          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
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+            units: MICROMOLE
+          }
+        }
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+          value: "CS(=O)C"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 3
+    }
+  }
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+      details: "96 Glass Vials"
+      material {
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+      }
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+        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
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+        }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+          volume {
+            value: 5.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+      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"
+        }
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+            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."
+    }
+  }
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+}
+reactions {
+  inputs {
+    key: "Amine"
+    value {
+      components {
+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+        is_limiting: false
+      }
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+        identifiers {
+          type: SMILES
+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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+        }
+        reaction_role: REAGENT
+      }
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+        identifiers {
+          type: SMILES
+          value: "[Cu]I"
+        }
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+          moles {
+            value: 0.25
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+          type: SMILES
+          value: "CS(=O)C"
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+            value: 12.5
+            units: MICROLITER
+          }
+          volume_includes_solutes: true
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+    key: "Aryl Halide"
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+        identifiers {
+          type: SMILES
+          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
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+      }
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+            units: MICROMOLE
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+        reaction_role: SOLVENT
+      }
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
+      }
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+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+        type: DRY_ALUMINUM_PLATE
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+        units: CELSIUS
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
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+  }
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+    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"
+        }
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+            units: MICROLITER
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+        }
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+      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"
+        }
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+            value: 0.5
+            units: MICROMOLE
+          }
+        }
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+  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
+      }
+    }
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+    reaction_time {
+      value: 18.0
+      units: HOUR
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+      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"
+}
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+        identifiers {
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+            value: 3.75
+            units: MICROMOLE
+          }
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+        identifiers {
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+            value: 7.5
+            units: MICROMOLE
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+        reaction_role: REAGENT
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+          type: SMILES
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+        reaction_role: CATALYST
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+          value: "CS(=O)C"
+        }
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+    key: "Aryl Halide"
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+        is_limiting: true
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+          type: SMILES
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+            units: MICROLITER
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+      volume {
+        value: 250.0
+        units: MICROLITER
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+        value: 80.0
+        units: CELSIUS
+      }
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+    type: ADDITION
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+      components {
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+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
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+        }
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+            units: MICROMOLE
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+        reaction_role: INTERNAL_STANDARD
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+    }
+  }
+  workups {
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+        value: 25.0
+        units: MICROLITER
+      }
+    }
+  }
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+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
+    input {
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
+        }
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+            units: MICROLITER
+          }
+        }
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+      units: HOUR
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+      }
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+        is_normalized: true
+        uses_authentic_standard: false
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+          value: 59.94
+        }
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
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+        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"
+}
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+  inputs {
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+          type: SMILES
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+        }
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+        }
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+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
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+          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
+        }
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+            units: MICROMOLE
+          }
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+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
+    value {
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+        identifiers {
+          type: SMILES
+          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
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+          }
+        }
+        reaction_role: CATALYST
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+      }
+      addition_order: 3
+    }
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
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+        units: MICROLITER
+      }
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+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
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+      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
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+        }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+          volume {
+            value: 5.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+      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"
+        }
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+            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 {
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+            value: 700.0
+            units: MICROLITER
+          }
+        }
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+      }
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+      value: 18.0
+      units: HOUR
+    }
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+      identifiers {
+        type: SMILES
+        value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5"
+      }
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+      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."
+    }
+  }
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+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+          details: "NAME resolved by the PubChem API"
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+        }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+    details: "25 microliter of resulting solution is taken"
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+        units: MICROLITER
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+    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"
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+            units: MICROLITER
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+        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 {
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
+      value {
+        type: LCMS
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+        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"
+}
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
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+        type: GLASS
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+        units: MICROLITER
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+        units: CELSIUS
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
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+        units: MICROLITER
+      }
+    }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+      units: HOUR
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+        instrument_manufacturer: "Waters"
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+    }
+  }
+  provenance {
+    experimenter {
+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      time {
+        value: "6/2/2021, 8:10:58 AM"
+      }
+      person {
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+        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."
+    }
+  }
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+}
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+          value: "C1CCNCC1"
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+            units: MICROLITER
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+        }
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+      addition_order: 2
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+          value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4"
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+            units: MICROMOLE
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+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
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+            units: MICROLITER
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+        reaction_role: SOLVENT
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
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+      control {
+        type: DRY_ALUMINUM_PLATE
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+      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"
+        }
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+            units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            units: MICROLITER
+          }
+        }
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+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            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"
+        }
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+            units: MICROLITER
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+      }
+    }
+  }
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+        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
+      }
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+        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"
+        }
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+            units: MICROMOLE
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+        is_limiting: false
+      }
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+          type: SMILES
+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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+            units: MICROMOLE
+          }
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+        reaction_role: REAGENT
+      }
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+        identifiers {
+          type: SMILES
+          value: "[Cu]I"
+        }
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+          moles {
+            value: 0.25
+            units: MICROMOLE
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+        reaction_role: CATALYST
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+          type: SMILES
+          value: "CS(=O)C"
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+    key: "Aryl Halide"
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+        identifiers {
+          type: SMILES
+          value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br"
+        }
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+            units: MICROMOLE
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+        reaction_role: REACTANT
+        is_limiting: true
+      }
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+    }
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+          type: SMILES
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+            units: MICROMOLE
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+            units: MICROLITER
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+        reaction_role: SOLVENT
+      }
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+      details: "96 Glass Vials"
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+        type: GLASS
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+        value: 250.0
+        units: MICROLITER
+      }
+    }
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+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+      }
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+        units: CELSIUS
+      }
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
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+    type: ADDITION
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+    input {
+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
+        }
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+          volume {
+            value: 95.0
+            units: MICROLITER
+          }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            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"
+        }
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+            value: 0.5
+            units: MICROMOLE
+          }
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+      }
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+  }
+  workups {
+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
+    amount {
+      volume {
+        value: 25.0
+        units: MICROLITER
+      }
+    }
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+  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"
+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
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+      value: 18.0
+      units: HOUR
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+      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"
+}
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+        identifiers {
+          type: SMILES
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+        }
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+            units: MICROMOLE
+          }
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+        reaction_role: REACTANT
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REAGENT
+      }
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+          type: SMILES
+          value: "[Cu]I"
+        }
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+            units: MICROMOLE
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+        }
+        reaction_role: CATALYST
+      }
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+          type: SMILES
+          value: "CS(=O)C"
+        }
+        amount {
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
+  }
+  inputs {
+    key: "Aryl Halide"
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+      components {
+        identifiers {
+          type: SMILES
+          value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
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+          type: SMILES
+          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
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+            units: MICROMOLE
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+            units: MICROLITER
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+        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"
+        }
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+            units: MICROLITER
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+          value: "CC(=O)O"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: INTERNAL_STANDARD
+      }
+    }
+  }
+  workups {
+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
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+      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"
+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
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+      value: 18.0
+      units: HOUR
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+    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 {
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+    value {
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+            units: MICROMOLE
+          }
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+        reaction_role: REACTANT
+        is_limiting: false
+      }
+      components {
+        identifiers {
+          type: SMILES
+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REAGENT
+      }
+      components {
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+          type: SMILES
+          value: "[Cu]I"
+        }
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+            value: 0.25
+            units: MICROMOLE
+          }
+        }
+        reaction_role: CATALYST
+      }
+      components {
+        identifiers {
+          type: SMILES
+          value: "CS(=O)C"
+        }
+        amount {
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+            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"
+        }
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+            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"
+        }
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+            value: 0.5
+            units: MICROMOLE
+          }
+        }
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+      }
+      components {
+        identifiers {
+          type: SMILES
+          value: "CS(=O)C"
+        }
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+            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"
+        }
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+          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"
+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          type: SMILES
+          value: "[Cu]I"
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+            units: MICROMOLE
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+            units: MICROLITER
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+            units: MICROLITER
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+          details: "NAME resolved by the PubChem API"
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+    input {
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      }
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+      units: HOUR
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+      }
+      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 {
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+      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."
+    }
+  }
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+}
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+        }
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+            value: 12.5
+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+          value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br"
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+            units: MICROMOLE
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+      }
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+    }
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+        value: 250.0
+        units: MICROLITER
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+        units: CELSIUS
+      }
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+      details: "Magnetic Stir Bar"
+    }
+  }
+  workups {
+    type: ADDITION
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+          details: "NAME resolved by the PubChem API"
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+        identifiers {
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROMOLE
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+        value: 25.0
+        units: MICROLITER
+      }
+    }
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+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
+    input {
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      units: HOUR
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+        }
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+      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 {
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+          value: "C1CCNCC1"
+        }
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+            units: MICROMOLE
+          }
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+        is_limiting: false
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+        reaction_role: REAGENT
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+          value: "[Cu]I"
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+            units: MICROMOLE
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+      }
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+        identifiers {
+          type: SMILES
+          value: "CS(=O)C"
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+            units: MICROLITER
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
+  }
+  inputs {
+    key: "Aryl Halide"
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+          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
+        }
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+            value: 2.5
+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
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+          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
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+          value: "CS(=O)C"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 3
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
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+    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"
+        }
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+          volume {
+            value: 95.0
+            units: MICROLITER
+          }
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+        reaction_role: WORKUP
+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            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"
+        }
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+            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
+          }
+        }
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+      }
+    }
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+      value: 18.0
+      units: HOUR
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+      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
+        }
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+      reaction_role: PRODUCT
+    }
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+      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."
+    }
+  }
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+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+      components {
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+          type: SMILES
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+            value: 700.0
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+      is_desired_product: true
+      measurements {
+        analysis_key: "UPLC-MS"
+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
+      }
+      reaction_role: PRODUCT
+    }
+    analyses {
+      key: "UPLC-MS"
+      value {
+        type: LCMS
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+        instrument_manufacturer: "Waters"
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+    }
+  }
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+    experimenter {
+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    city: "Rahway, NJ"
+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      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"
+}
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+        }
+        reaction_role: SOLVENT
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+      addition_order: 2
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+            units: MICROMOLE
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+        units: MICROLITER
+      }
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+          type: SMILES
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+        is_normalized: true
+        uses_authentic_standard: false
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+        instrument_manufacturer: "Waters"
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
+    }
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+      }
+      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."
+    }
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+}
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+            units: MICROMOLE
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
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+      }
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+      details: "96 Glass Vials"
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+        units: MICROLITER
+      }
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+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+        type: DRY_ALUMINUM_PLATE
+      }
+      setpoint {
+        value: 80.0
+        units: CELSIUS
+      }
+    }
+    stirring {
+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
+  }
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+    type: ADDITION
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+    input {
+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
+          }
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+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
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+          details: "NAME resolved by the PubChem API"
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+        }
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+            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"
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+            units: MICROLITER
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+      }
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+      measurements {
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+        }
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+      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"
+        }
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+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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+            units: MICROMOLE
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+        reaction_role: REAGENT
+      }
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+          type: SMILES
+          value: "[Cu]I"
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+            value: 0.25
+            units: MICROMOLE
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
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+        reaction_role: SOLVENT
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+      addition_order: 2
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+          type: SMILES
+          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
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+            units: MICROMOLE
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+            units: MICROLITER
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+        reaction_role: SOLVENT
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+      details: "96 Glass Vials"
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+        type: GLASS
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+        value: 250.0
+        units: MICROLITER
+      }
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+      details: "Nitrogen Filled"
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+    type: ADDITION
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+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
+        }
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+            units: MICROLITER
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+        }
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+            value: 5.0
+            units: MICROLITER
+          }
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+        identifiers {
+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            units: MICROMOLE
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+  workups {
+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
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+        units: MICROLITER
+      }
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+    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"
+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
+          }
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+        reaction_role: WORKUP
+      }
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+      units: HOUR
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+        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
+    }
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+      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"
+}
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+        }
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+            units: MICROMOLE
+          }
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+            units: MICROMOLE
+          }
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+        reaction_role: REAGENT
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+          type: SMILES
+          value: "[Cu]I"
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+            units: MICROMOLE
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+        }
+        reaction_role: CATALYST
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+          value: "CS(=O)C"
+        }
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+            units: MICROLITER
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
+  }
+  inputs {
+    key: "Aryl Halide"
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+        identifiers {
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+          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
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+          type: SMILES
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
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+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+      setpoint {
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+        units: CELSIUS
+      }
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+    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"
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+            units: MICROLITER
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+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROLITER
+          }
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+        reaction_role: WORKUP
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+        identifiers {
+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROMOLE
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+        }
+        reaction_role: INTERNAL_STANDARD
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+    }
+  }
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+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
+    amount {
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+        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"
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+            units: MICROLITER
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+        reaction_role: WORKUP
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+      units: HOUR
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+        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
+      }
+      is_desired_product: true
+      measurements {
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+        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 {
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+            units: MICROMOLE
+          }
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+        is_limiting: false
+      }
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+          type: SMILES
+          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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+        reaction_role: REAGENT
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+          value: "[Cu]I"
+        }
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+            units: MICROMOLE
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+      }
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+          value: "CS(=O)C"
+        }
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+            value: 12.5
+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+    key: "Aryl Halide"
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+      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"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
+    value {
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+          type: SMILES
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+        }
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+            units: MICROMOLE
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+        }
+        reaction_role: CATALYST
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+          type: SMILES
+          value: "CS(=O)C"
+        }
+        amount {
+          volume {
+            value: 12.5
+            units: MICROLITER
+          }
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 3
+    }
+  }
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
+  conditions {
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+      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"
+        }
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+            value: 95.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            value: 5.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+      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"
+        }
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+          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"
+        }
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+            value: 700.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
+  }
+  outcomes {
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+      value: 18.0
+      units: HOUR
+    }
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+      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."
+    }
+  }
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+}
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+  inputs {
+    key: "Amine"
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          value: "[Cu]I"
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+            units: MICROLITER
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+        units: MICROLITER
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+          details: "NAME resolved by the PubChem API"
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+        }
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+        }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+        identifiers {
+          type: SMILES
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+            units: MICROLITER
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+      is_desired_product: true
+      measurements {
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+        }
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+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
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+        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"
+}
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+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
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+      addition_order: 2
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
+    }
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+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
+      }
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+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      units: HOUR
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+        is_normalized: true
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+        percentage {
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+        }
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+      reaction_role: PRODUCT
+    }
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+      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 {
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      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."
+    }
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+}
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+            units: MICROLITER
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+      addition_order: 2
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+          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
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+            units: MICROMOLE
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+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
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+            units: MICROLITER
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+        reaction_role: SOLVENT
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+      details: "96 Glass Vials"
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+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+        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"
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            units: MICROLITER
+          }
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROMOLE
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+        }
+        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"
+        }
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+            units: MICROLITER
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+        reaction_role: WORKUP
+      }
+    }
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+      units: HOUR
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+      }
+      is_desired_product: true
+      measurements {
+        analysis_key: "UPLC-MS"
+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      reaction_role: PRODUCT
+    }
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+      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."
+    }
+  }
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+}
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+  inputs {
+    key: "Amine"
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          volume_includes_solutes: true
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+        units: MICROLITER
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+        units: CELSIUS
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+          details: "NAME resolved by the PubChem API"
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+          type: SMILES
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+      }
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+        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"
+      }
+    }
+  }
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+    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."
+    }
+  }
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+}
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
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+      addition_order: 2
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+        units: CELSIUS
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+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
+      }
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+          type: SMILES
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+        is_normalized: true
+        uses_authentic_standard: false
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+      reaction_role: PRODUCT
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+        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)"
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+      }
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+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
+    }
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+    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."
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+}
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+        }
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+        }
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+        identifiers {
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
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+    }
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+        }
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+      }
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+      details: "96 Glass Vials"
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+        units: MICROLITER
+      }
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+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
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+      control {
+        type: DRY_ALUMINUM_PLATE
+      }
+      setpoint {
+        value: 80.0
+        units: CELSIUS
+      }
+    }
+    stirring {
+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
+  }
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+    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 {
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+          value: "1,3,5-trimethoxybenzene"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: INTERNAL_STANDARD
+      }
+    }
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+    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"
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+            units: MICROLITER
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+      }
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+      measurements {
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+    }
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+      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"
+}
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+  inputs {
+    key: "Amine"
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          value: "[Cu]I"
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+            units: MICROLITER
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+          value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br"
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+        units: MICROLITER
+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      units: HOUR
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+      measurements {
+        analysis_key: "UPLC-MS"
+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
+          value: 2.0
+        }
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+      reaction_role: PRODUCT
+    }
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+      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"
+}
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+          value: "[Cu]I"
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+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+        identifiers {
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+        is_limiting: true
+      }
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+        units: MICROLITER
+      }
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+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
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+          type: SMILES
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+      units: HOUR
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+        is_normalized: true
+        uses_authentic_standard: false
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+        }
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+      reaction_role: PRODUCT
+    }
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+        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"
+      }
+    }
+  }
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+    experimenter {
+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
+    }
+    city: "Rahway, NJ"
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+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      time {
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+      }
+      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."
+    }
+  }
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+}
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+        }
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+          }
+          volume_includes_solutes: true
+        }
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+        }
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+            units: MICROMOLE
+          }
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+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
+    value {
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+          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
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+            units: MICROMOLE
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+          value: "CS(=O)C"
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+        reaction_role: SOLVENT
+      }
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+      details: "96 Glass Vials"
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+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+    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"
+        }
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+            units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+          volume {
+            value: 5.0
+            units: MICROLITER
+          }
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+        identifiers {
+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            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"
+        }
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+            units: MICROLITER
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+      value: 18.0
+      units: HOUR
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+      identifiers {
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+        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
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+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+      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"
+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          value: "[Cu]I"
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+            units: MICROLITER
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+          volume_includes_solutes: true
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
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+        units: CELSIUS
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+          details: "NAME resolved by the PubChem API"
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+        }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+          type: SMILES
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+      }
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+      measurements {
+        analysis_key: "UPLC-MS"
+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+          value: 28.8
+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
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+        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 {
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+      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."
+    }
+  }
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+}
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+        }
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
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+      addition_order: 2
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+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+  }
+  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."
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROMOLE
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+        units: MICROLITER
+      }
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+        value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5"
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+      reaction_role: PRODUCT
+    }
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+        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"
+      }
+    }
+  }
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+    experimenter {
+      name: "Spencer Dreher"
+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
+      email: "spencer_dreher@merck.com"
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+    doi: "10.1039/C5SC04751J"
+    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
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+      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."
+    }
+  }
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+}
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+        }
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+            units: MICROMOLE
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+      }
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+          value: "CS(=O)C"
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+          volume_includes_solutes: true
+        }
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+      }
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+    key: "Aryl Halide"
+    value {
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+          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
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+        }
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+            units: MICROLITER
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+      }
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
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+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+      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"
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+            units: MICROLITER
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROLITER
+          }
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+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            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"
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+            units: MICROLITER
+          }
+        }
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+      units: HOUR
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+        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
+      }
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
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+    }
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+      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"
+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+        identifiers {
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+          value: "[Cu]I"
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+          moles {
+            value: 0.25
+            units: MICROMOLE
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+            units: MICROLITER
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+          volume_includes_solutes: true
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+      addition_order: 2
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+            units: MICROMOLE
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
+      }
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+    type: ADDITION
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+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
+        }
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+            units: MICROLITER
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+        }
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+            units: MICROLITER
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+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+            units: MICROMOLE
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+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
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+        units: MICROLITER
+      }
+    }
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+    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"
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+        }
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+          volume {
+            value: 700.0
+            units: MICROLITER
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+      }
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+      units: HOUR
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+        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"
+}
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+            units: MICROMOLE
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+        reaction_role: REAGENT
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+          value: "[Cu]I"
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+            units: MICROMOLE
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+        }
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+          value: "CS(=O)C"
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+            units: MICROLITER
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+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
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+            units: MICROMOLE
+          }
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
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+        value: 250.0
+        units: MICROLITER
+      }
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+      details: "Nitrogen Filled"
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+        type: DRY_ALUMINUM_PLATE
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+        units: CELSIUS
+      }
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
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+  }
+  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."
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+            units: MICROLITER
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+          value: "1,3,5-trimethoxybenzene"
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+          details: "NAME resolved by the PubChem API"
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+            units: MICROMOLE
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+        units: MICROLITER
+      }
+    }
+  }
+  workups {
+    type: ADDITION
+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
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+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      units: HOUR
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+        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
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+      is_desired_product: true
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+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
+      value {
+        type: LCMS
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+        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"
+}
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+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+            units: MICROMOLE
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+      }
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+          value: "[Cu]I"
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+            units: MICROMOLE
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+          value: "CS(=O)C"
+        }
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+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
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+      addition_order: 2
+    }
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+    key: "Aryl Halide"
+    value {
+      components {
+        identifiers {
+          type: SMILES
+          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
+        }
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+            value: 2.5
+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
+    value {
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+          value: "CS(=O)C"
+        }
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+            units: MICROLITER
+          }
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+        reaction_role: SOLVENT
+      }
+      addition_order: 3
+    }
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
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+        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"
+        }
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+            value: 95.0
+            units: MICROLITER
+          }
+        }
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+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            value: 5.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
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+        identifiers {
+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            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"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
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+      value: 18.0
+      units: HOUR
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+      identifiers {
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+        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 {
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      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"
+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          type: SMILES
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+        identifiers {
+          type: SMILES
+          value: "[Cu]I"
+        }
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+          moles {
+            value: 0.25
+            units: MICROMOLE
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
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+        reaction_role: SOLVENT
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+      addition_order: 2
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+          type: SMILES
+          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
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+            units: MICROMOLE
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+            units: MICROLITER
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
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+        units: CELSIUS
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+      details: "Magnetic Stir Bar"
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROLITER
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+            units: MICROLITER
+          }
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+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
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+    details: "25 microliter of resulting solution is taken"
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+        value: 25.0
+        units: MICROLITER
+      }
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+    input {
+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC#N"
+        }
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+            value: 700.0
+            units: MICROLITER
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+      units: HOUR
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+        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
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+      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
+    }
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+      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"
+}
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+            units: MICROMOLE
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+            units: MICROMOLE
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+        reaction_role: REAGENT
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+          value: "[Cu]I"
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+          volume_includes_solutes: true
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+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
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+            units: MICROMOLE
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+        is_limiting: true
+      }
+      addition_order: 1
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+          type: SMILES
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+            units: MICROLITER
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+      details: "96 Glass Vials"
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+        type: GLASS
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+        value: 250.0
+        units: MICROLITER
+      }
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+      details: "Nitrogen Filled"
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+        units: CELSIUS
+      }
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
+  }
+  workups {
+    type: ADDITION
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+      components {
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+          details: "NAME resolved by the PubChem API"
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+          }
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+          value: "1,3,5-trimethoxybenzene"
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        }
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+            units: MICROMOLE
+          }
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+        reaction_role: INTERNAL_STANDARD
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+    }
+  }
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+    type: ALIQUOT
+    details: "25 microliter of resulting solution is taken"
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+        units: MICROLITER
+      }
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+  }
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+    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"
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+            units: MICROLITER
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+        reaction_role: WORKUP
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+      units: HOUR
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+      }
+      is_desired_product: true
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      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"
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+      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."
+    }
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+}
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+          value: "C1CCNCC1"
+        }
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+      }
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
+    }
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+          type: SMILES
+          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
+        }
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+            units: MICROMOLE
+          }
+        }
+        reaction_role: REACTANT
+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
+    value {
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+          type: SMILES
+          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
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+          value: "CS(=O)C"
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+            units: MICROLITER
+          }
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 3
+    }
+  }
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+      details: "96 Glass Vials"
+      material {
+        type: GLASS
+      }
+      volume {
+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
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+    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"
+        }
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+            units: MICROLITER
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+        }
+        reaction_role: WORKUP
+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            value: 5.0
+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
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+        identifiers {
+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            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"
+        }
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+            units: MICROLITER
+          }
+        }
+        reaction_role: WORKUP
+      }
+    }
+  }
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+      units: HOUR
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+      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 {
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+        }
+      }
+      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"
+}
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+  inputs {
+    key: "Amine"
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+        identifiers {
+          type: SMILES
+          value: "C1CCNCC1"
+        }
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+          type: SMILES
+          value: "[Cu]I"
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+            units: MICROMOLE
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+            units: MICROLITER
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+          volume_includes_solutes: true
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+          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
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+      details: "96 Glass Vials"
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+        units: MICROLITER
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+          details: "NAME resolved by the PubChem API"
+          value: "CS(C)=O"
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
+      }
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+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      }
+      is_desired_product: true
+      measurements {
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+        }
+      }
+      reaction_role: PRODUCT
+    }
+    analyses {
+      key: "UPLC-MS"
+      value {
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+        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"
+}
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+          value: "CS(=O)C"
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
+        reaction_role: SOLVENT
+      }
+      addition_order: 2
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+        type: GLASS
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+        value: 250.0
+        units: MICROLITER
+      }
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+      details: "Nitrogen Filled"
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+      setpoint {
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+        units: CELSIUS
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+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
+  }
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+    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."
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+            units: MICROLITER
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+        }
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+            units: MICROMOLE
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+        value: 25.0
+        units: MICROLITER
+      }
+    }
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+    type: ADDITION
+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
+    input {
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+            units: MICROLITER
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+      units: HOUR
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+        is_normalized: true
+        uses_authentic_standard: false
+        percentage {
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      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."
+    }
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+}
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+          value: "C1CCNCC1"
+        }
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+      }
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+            units: MICROLITER
+          }
+          volume_includes_solutes: true
+        }
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+          type: SMILES
+          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
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+            units: MICROMOLE
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+        is_limiting: true
+      }
+      addition_order: 1
+    }
+  }
+  inputs {
+    key: "Catalyst"
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+          type: SMILES
+          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
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+            units: MICROMOLE
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+          value: "CS(=O)C"
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+            units: MICROLITER
+          }
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+        reaction_role: SOLVENT
+      }
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+      details: "96 Glass Vials"
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+        value: 250.0
+        units: MICROLITER
+      }
+    }
+    environment {
+      type: GLOVE_BOX
+      details: "Nitrogen Filled"
+    }
+  }
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+      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"
+        }
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+          details: "NAME resolved by the PubChem API"
+          value: "CC(=O)O"
+        }
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+            units: MICROLITER
+          }
+        }
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+      }
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+        identifiers {
+          type: NAME
+          value: "1,3,5-trimethoxybenzene"
+        }
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
+          value: "COc1cc(OC)cc(OC)c1"
+        }
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+            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"
+        }
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+            units: MICROLITER
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+        }
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+      }
+    }
+  }
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+      units: HOUR
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+        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 {
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+        }
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+      reaction_role: PRODUCT
+    }
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+      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."
+    }
+  }
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+}
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+  inputs {
+    key: "Amine"
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+        units: MICROLITER
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+          details: "NAME resolved by the PubChem API"
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+        units: MICROLITER
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+        type: YIELD
+        uses_internal_standard: true
+        is_normalized: true
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+        }
+      }
+      reaction_role: PRODUCT
+    }
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+      key: "UPLC-MS"
+      value {
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+        instrument_manufacturer: "Waters"
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+    }
+  }
+  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"
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+      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."
+    }
+  }
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+}
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+          }
+          volume_includes_solutes: true
+        }
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+            units: MICROMOLE
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+        units: MICROLITER
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+      orcid: "0000-0002-5094-1218"
+      organization: "Merck"
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+      time {
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+      }
+      person {
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+        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."
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+}
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+        }
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+        is_limiting: true
+      }
+      addition_order: 1
+    }
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+        units: MICROLITER
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+      details: "Nitrogen Filled"
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+      }
+      setpoint {
+        value: 80.0
+        units: CELSIUS
+      }
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+    stirring {
+      type: STIR_BAR
+      details: "Magnetic Stir Bar"
+    }
+  }
+  workups {
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+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+          details: "NAME resolved by the PubChem API"
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+          }
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+        }
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+        }
+        reaction_role: INTERNAL_STANDARD
+      }
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+    amount {
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+        value: 25.0
+        units: MICROLITER
+      }
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+  workups {
+    type: ADDITION
+    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
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+      components {
+        identifiers {
+          type: SMILES
+          details: "NAME resolved by the PubChem API"
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+        uses_internal_standard: true
+        is_normalized: true
+        uses_authentic_standard: false
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+      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"
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