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0
US05849732
COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)Nc1cc(OC)cc(C(C)(C)C)c1O
None specified
NA
COC(=O)[C@H](CCCCN)NC(=O)Nc1cc(OC)cc(C(C)(C)C)c1O
# Reaction Trace: Cbz (Benzyloxycarbonyl) Deprotection ## 1. Reaction Type **Cbz deprotection (hydrogenolysis)** — a reductive cleavage of a benzyl carbamate protecting group. Classified as a **protecting group removal**, typically effected by catalytic hydrogenation (H₂, Pd/C) or, alternatively, strong acid (HBr/AcOH...
Deprotection of Cbz (benzyloxycarbonyl) group on lysine side chain. Typically hydrogenolysis with H2/Pd-C. Provide trace.
moonshotai/Kimi-K3
low
379
599
deprotections
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1
US20120114765A1
O=C(O)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1
Nc1cccc2cnccc12
NA
O=C(Nc1cccc2cnccc12)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1
## Reaction Trace **1. Reaction type:** Amide bond formation (peptide-type coupling) — a carboxylic acid is condensed with a primary aromatic amine (5-aminoisoquinoline) to give a carboxamide. Classified as a nucleophilic acyl substitution / condensation. **2. Transformation:** - **Broken:** The C–OH bond of the thio...
Amide bond formation from carboxylic acid and 5-aminoisoquinoline.
moonshotai/Kimi-K3
low
374
550
acylation
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2
US08003648B2
Cc1nc(-c2ccc(C=O)cc2)sc1COc1ccc([C@H](CC(=O)N2C(=O)OC[C@@H]2Cc2ccccc2)c2ccon2)cc1
CCNCC
NA
CCN(CC)Cc1ccc(-c2nc(C)c(COc3ccc([C@H](CC(=O)N4C(=O)OC[C@@H]4Cc4ccccc4)c4ccon4)cc3)s2)cc1
1. **Reaction type**: Reductive amination of an aryl aldehyde with a secondary amine, giving a benzylic tertiary amine. More specifically: Ar–CHO + Et₂NH → Ar–CH₂–NEt₂. The listed conditions omit the reductant, but the net transformation requires iminium reduction. 2. **Transformation**: The aldehyde C=O is converted ...
The user wants a reaction trace for conversion of an aryl aldehyde to tertiary amine using diethylamine. This is reductive amination? Wait reagents only CCNCC (diethylamine) listed, no reducing agent specified. Product shows aldehyde Ar-CHO converted to Ar-CH2-N(Et)2. That requires reductive amination (aldehyde + secon...
moonshotai/Kimi-K3
low
417
778
heteroatom_alkylation_arylation
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3
US09045475B2
O=C(CF)CF
CC1(C)CCC(CN2CCN(c3ccc(C(=O)NS(=O)(=O)c4ccc(NCC5CNC5)c([N+](=O)[O-])c4)c(Oc4cnc5[nH]ccc5c4)c3)CC2)=C(c2ccc(Cl)cc2)C1
NA
CC1(C)CCC(CN2CCN(c3ccc(C(=O)NS(=O)(=O)c4ccc(NCC5CN(C(CF)CF)C5)c([N+](=O)[O-])c4)c(Oc4cnc5[nH]ccc5c4)c3)CC2)=C(c2ccc(Cl)cc2)C1
1. **Reaction type**: Reductive amination / N-alkylation of a secondary azetidine with a ketone. More specifically, installation of a **1,3-difluoroisopropyl** group on the azetidine nitrogen using 1,3-difluoroacetone as a carbonyl electrophile; reductant/acid are implied by “NA.” 2. **Transformation**: The azetidine ...
The user wants a reaction trace. Need analyze chemistry. Starting material O=C(CF)CF = 1,3-difluoroacetone (DFA), carbonyl compound. Reagent is complex tertiary aniline-bearing azetidine? Product shows an azetidine N alkylation: reagent has ...NCC5CNC5 (an azetidine ring with NH and CH2NH linker?). Product NCC5CN(C(CF...
moonshotai/Kimi-K3
low
469
1,164
heteroatom_alkylation_arylation
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4
US08188098B2
O=C(Cl)OC1CCCC1
CCOc1ccc(Oc2ncnc3c2cnn3C2CCNCC2)c(F)c1
NA
CCOc1ccc(Oc2ncnc3c2cnn3C2CCN(C(=O)OC3CCCC3)CC2)c(F)c1
**1. Reaction type:** N-Acylation via chloroformate — carbamate (urethane) formation. A nucleophilic substitution at an acyl carbon (addition–elimination). **2. Transformation:** The C–Cl bond of cyclopentyl chloroformate is broken and a new N–C(=O) bond is formed. The secondary amine (piperidine N–H) of the pyrazolo-...
Carbamate formation: piperidine N attacks chloroformate.
moonshotai/Kimi-K3
low
368
560
acylation
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5
US20140275084A1
Cn1cnc(-c2cc(C#N)ccn2)c1Br
OB(O)c1ccc(-n2cccn2)cc1
NA
Cn1cnc(-c2cc(C#N)ccn2)c1-c1ccc(-n2cccn2)cc1
# Reaction Trace ## 1. Reaction Type **Suzuki–Miyaura cross-coupling** — a palladium-catalyzed sp²–sp² carbon–carbon bond formation between an aryl (heteroaryl) halide and an arylboronic acid. ## 2. Transformation - **Bond broken:** C–Br bond on the bromoimidazole (C5 of the N-methylimidazole ring); B–C bond cleavage...
Suzuki coupling aryl bromide + boronic acid.
moonshotai/Kimi-K3
low
362
609
cc_bond_formation
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6
US20110224204A1
N#Cc1ccc(OC2CCCCO2)c(Br)c1
CC1(C)OB(c2ccc(OCc3ccc4ccccc4n3)cc2)OC1(C)C
NA
N#Cc1ccc(OC2CCCCO2)c(-c2ccc(OCc3ccc4ccccc4n3)cc2)c1
### 1. Reaction type **Suzuki–Miyaura cross-coupling** of an **aryl bromide** with an **aryl pinacol boronate** to form a biaryl bond. ### 2. Transformation - **Bond broken:** The aryl–Br bond in 3-bromo-4-(tetrahydropyran-2-yloxy)benzonitrile. - **Bond formed:** A new **C(sp²)–C(sp²)** bond between the brominated ary...
We need need infer conditions absent. Suzuki. Starting aryl bromide + pinacol boronate. Mechanism Pd cycle. mention base, catalyst, solvent needed though not listed. Regio Br replaced. Product nitrile, THP ether, quinoline ether unchanged.
moonshotai/Kimi-K3
low
375
615
cc_bond_formation
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7
US20130005716A1
COc1ccc(C(=O)Cc2c(Cl)c[n+]([O-])cc2Cl)c2c1OC1(CCCC1)O2
None specified
NA
COc1ccc(C(O)Cc2c(Cl)c[n+]([O-])cc2Cl)c2c1OC1(CCCC1)O2
1. **Reaction type**: Chemoselective ketone reduction to a secondary alcohol — hydride reduction/nucleophilic addition to a carbonyl, typically NaBH₄ or LiAlH₄ followed by protic workup. The aryl ketone is reduced while the pyridine N-oxide, aryl chlorides, methoxy group, and spiroketal remain intact. 2. **Transformat...
The user wants a reaction trace for reduction of an aryl ketone to secondary benzylic alcohol. Starting: COc1ccc(C(=O)Cc2...)c2c1... product C(O)C... Ketone C=O reduced to CH-OH, alpha methylene unchanged. No reagents specified; typical NaBH4 or borane reduction. Need cover reaction type, transformation, mechanism, rea...
moonshotai/Kimi-K3
low
373
768
reductions
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8
US20130172384A1
O=C(O)c1ccc(Br)cc1Cl
CC(C)(C)OC(=O)NN
NA
CC(C)(C)OC(=O)NNC(=O)c1ccc(Br)cc1Cl
# Reaction Trace: Acyl Hydrazide Formation (Amide Coupling) ## 1. Reaction Type **Amide bond formation (carboxylic acid–hydrazide condensation)** — specifically, coupling of a carboxylic acid with a mono-Boc-protected hydrazine (tert-butyl carbazate) to give an **N′-acyl-N-Boc-hydrazide**. ## 2. Transformation - **Bo...
Acid + Boc-hydrazide → acyl hydrazide. Conditions NA, but amide coupling (needs coupling reagent typically; note this).
moonshotai/Kimi-K3
low
346
647
acylation
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9
US20050277619A1
Nc1ncnc2c1nc(CBr)n2CCc1ccccc1
CCOP(=O)(CO)OCC
NA
CCOP(=O)(COCc1nc2c(N)ncnc2n1CCc1ccccc1)OCC
## Reaction Trace **1. Reaction Type** Williamson ether synthesis (O-alkylation / SN2 alkylation of a hydroxymethylphosphonate with a benzylic/heterobenzylic bromide). **2. Transformation** The C–Br bond of the (bromomethyl)purine is broken and a new C–O bond is formed between that methylene carbon and the oxygen of ...
This is an Arbuzov-like alkylation: bromomethyl imidazopurine + hydroxymethyl phosphonate? Actually reagent is diethyl hydroxymethylphosphonate, and product has P-CH2-O-CH2-imidazole? Wait product: CCOP(=O)(COCc1...) — phosphonate carbon is C-O-CH2-aryl. Starting CBr (CH2Br) plus P-CH2OH: O alkylation of hydroxymethylp...
moonshotai/Kimi-K3
low
357
648
heteroatom_alkylation_arylation
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10
US20110263607A1
CC(C)(C)OC(=O)CONC(=O)NCc1cccc2ccccc12
None specified
NA
O=C(O)CONC(=O)NCc1cccc2ccccc12
1. **Reaction type**: Acid-promoted **tert-butyl ester deprotection** / protecting-group cleavage, converting a tert-butyl ester into the corresponding carboxylic acid. Commonly run with TFA/CH₂Cl₂, HCl/dioxane, or formic acid; here the reagent line is unspecified, but the transformation is diagnostic of tBu ester acid...
Starting material: tert-butyl ester Boc-like? Actually CC(C)(C)OC(=O)CONC(=O)NCH2-naphthyl. Product carboxylic acid O=C(O)CON... This is deprotection of tert-butyl ester to carboxylic acid. Reagents none specified likely TFA/DCM or acid. Need trace. Need produce final 150-300 words. Include acidolytic cleavage tert-but...
moonshotai/Kimi-K3
low
343
885
deprotections
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11
US06372735B1
CCOC(=O)c1nnn(Cc2ccc(OC)cc2)c1C(=O)c1ccc(OC)c(OC)c1
None specified
NA
CCOC(=O)c1nn[nH]c1C(=O)c1ccc(OC)c(OC)c1
## 1. Reaction type **N–PMB deprotection (protecting-group removal)** of a triazole nitrogen. The *p*-methoxybenzyl (PMB) group is cleaved to give the **NH triazole** without affecting the ethyl ester, ketone, or aryl methoxy groups. ## 2. Transformation - **Bond broken:** triazole **N–CH₂** bond of the PMB group. - *...
We need need infer deprotection of PMB from triazole. Reagents unspecified. Need caveat likely oxidative/deprotecting. Product N-H triazole. Starting N-PMB. This is dealkylation. Mention typical CAN/TFA/hydrogenolysis? PMB cleavage via DDQ oxidation to iminium then hydrolysis, or acid. For N-PMB on triazole perhaps TFA...
moonshotai/Kimi-K3
low
362
655
unclassified
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12
US20100003305A1
CC(C)[C@H](NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O
COC(=O)CN
NA
COC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(C)C
## Reaction Trace **1. Reaction Type** Peptide bond formation (amide coupling) — a nucleophilic acyl substitution of a carboxylic acid by an amine to form a peptide (amide) bond. **2. Transformation** The C-terminal carboxylic acid of the tetrapeptide Z-Val-Pro-Gly-Val-OH is converted into an amide with the α-amino g...
Peptide coupling: C-terminal carboxylic acid of Z-Val-Pro-Gly-Val-OH coupled with glycine methyl ester.
moonshotai/Kimi-K3
low
429
560
acylation
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13
US07820673B2
O=Cc1c[nH]cn1
NC1CCN(Cc2ccccc2)CC1
NA
c1ccc(CN2CCC(NCc3c[nH]cn3)CC2)cc1
## Reaction Trace **1. Reaction Type** Reductive amination of an aldehyde (imidazole-4-carbaldehyde) with a primary amine (1-benzylpiperidin-4-amine) to give a secondary amine. Classified as a condensation/reduction (C–N bond formation via imine intermediate). **2. Transformation** - Broken: C=O of the imidazole alde...
Aldehyde + amine → secondary amine = reductive amination. No reductant listed but net transformation clear.
moonshotai/Kimi-K3
low
344
569
heteroatom_alkylation_arylation
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14
US20050148627A1
BrCc1ccccc1
Oc1ccc(O)c(Br)c1
NA
Oc1ccc(OCc2ccccc2)c(Br)c1
# Reaction Trace **1. Reaction Type:** Williamson ether synthesis — specifically, *O*-alkylation of a phenol (monobenzylation of 2-bromohydroquinone). Classified as an SN2 reaction. **2. Transformation:** - **Broken:** C–Br bond of benzyl bromide (benzylic C–Br). - **Formed:** New C–O bond between one phenolic oxygen...
Williamson ether synthesis, regioselectivity: 4-benzyloxy phenol (monobenzylation), bromine present. Product: 2-bromo-4-benzyloxyphenol? Starting hydroquinone with Br at position 2; product mono-O-benzyl.
moonshotai/Kimi-K3
low
329
598
protections
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15
US20070225349A1
COc1ccc(-c2nn(C(C)C)c3c(Cl)cccc23)cc1
None specified
NA
CC(C)n1nc(-c2ccc(O)cc2)c2cccc(Cl)c21
# Reaction Trace: Aryl Methyl Ether Demethylation ## 1. Reaction Type **O-Demethylation of an aryl methyl ether (anisole cleavage)** — a deprotection reaction converting a 4-methoxyphenyl group to a free phenol. Typical reagents: BBr₃, BCl₃, or 48% HBr/AcOH at elevated temperature. ## 2. Transformation - **Bonds brok...
Anisole demethylation, likely BBr3.
moonshotai/Kimi-K3
low
344
670
unclassified
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16
US05834461
Cc1ccccc1C(=O)Cl
Nc1ccc(C(=O)N2Cc3ccccc3Sc3ncccc32)cc1
NA
Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccccc3Sc3ncccc32)cc1
# Reaction Trace: Amide Bond Formation via Acyl Substitution ## 1. Reaction Type **N-Acylation (amide formation) of a primary aniline with an acid chloride** — a nucleophilic acyl substitution (Schotten–Baumann-type coupling). The starting acid chloride is 2-methylbenzoyl chloride; the amine is an aniline bearing a fu...
Acid chloride + amine → amide (Schotten-Baumann type).
moonshotai/Kimi-K3
low
367
614
acylation
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17
US20150057271A1
Fc1ccc(C(F)(F)F)cc1Br
c1ccc2c(c1)NCCO2
NA
FC(F)(F)c1ccc(N2CCOc3ccccc32)c(Br)c1
## Reaction Trace **1. Reaction Type** Nucleophilic aromatic substitution (SNAr) — N-arylation of a secondary amine (3,4-dihydro-2H-1,4-benzoxazine) with an activated aryl halide. **2. Transformation** - Broken: C–F bond of the aryl fluoride; N–H bond of the benzoxazine. - Formed: new C(aryl)–N bond between the ring ...
Nucleophilic aromatic substitution on aryl fluoride para to CF3, with Br retained. 3,4-dihydro-2H-benzo[b][1,4]oxazine as nucleophile.
moonshotai/Kimi-K3
low
345
610
heteroatom_alkylation_arylation
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18
US05612288
Fc1cccnc1F
CC(C)S
NA
CC(C)Sc1ncccc1F
1. **Reaction type**: Regioselective **nucleophilic aromatic substitution (SNAr)** on an electron-poor heteroaryl fluoride; specifically thiolate substitution of 2,3-difluoropyridine at C2 to give a 2-(isopropylthio)-3-fluoropyridine. 2. **Transformation**: The **C2–F bond** of the difluoropyridine is broken and a new...
The user wants a reaction trace for nucleophilic aromatic substitution of 2,3-difluoropyridine? Starting Fc1cccnc1F = 2,3-difluoropyridine? SMILES F c1 c c c n c1 F: fluorines at 2 and 3? Product CC(C)Sc1ncccc1F means isopropylthio replaces F adjacent to N (2-position), leaving 3-F. Reaction with propane-2-thiol. Need ...
moonshotai/Kimi-K3
low
319
781
heteroatom_alkylation_arylation
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19
US20120202797A1
Cc1cc2n(c1)Cc1cc(Cl)ccc1N=C2Cl
COC(=O)C(C)(C)CN1CCNCC1
NA
COC(=O)C(C)(C)CN1CCN(C2=Nc3ccc(Cl)cc3Cn3cc(C)cc32)CC1
## Reaction Trace **1. Reaction type** Nucleophilic aromatic/heteroaromatic substitution (SNAr-type) — specifically, nucleophilic displacement of a vinylic/imidoyl chloride by a secondary amine. The piperazine nitrogen displaces chloride from the electron-deficient C=N–Cl (chloroimine) carbon of the fused pyrido-benzo...
SNAr / N-alkylation of amidine-like C-Cl with piperazine.
moonshotai/Kimi-K3
low
372
556
heteroatom_alkylation_arylation
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20
US05866589
CCN(c1nc(F)ccc1NC(C)C)C1CCN(Cc2ccccc2)CC1
None specified
NA
CCN(c1nc(F)ccc1NC(C)C)C1CCNCC1
# Reaction Trace: N-Debenzylation of Piperidine ## 1. Reaction Type **Hydrogenolytic N-debenzylation** — a reductive cleavage of a benzylic C–N bond, typically achieved by catalytic hydrogenation (H₂, Pd/C or Pd(OH)₂/C). This is a standard protecting-group removal (N-benzyl deprotection) in medicinal/heterocyclic chem...
N-debenzylation of piperidine. Hydrogenolysis.
moonshotai/Kimi-K3
low
348
611
unclassified
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21
US20110152240A1
O=Cc1cnn2c(NC3CC3)cc(NC3CCCC3)nc12
O=C1CNC(=O)N1
NA
O=C1NC(=O)/C(=C/c2cnn3c(NC4CC4)cc(NC4CCCC4)nc23)N1
## Reaction Trace: Knoevenagel Condensation to a 5-Arylidene Hydantoin **1. Reaction type** Knoevenagel condensation (specifically, a C-5 condensation of an active-methylene heterocycle — hydantoin — with an aromatic aldehyde), classified as a base-catalyzed aldol-type condensation with dehydration. **2. Transformati...
Aldehyde + hydantoin (imidazolidine-2,4-dione) → Knoevenagel condensation to 5-arylidene hydantoin.
moonshotai/Kimi-K3
low
367
565
cc_bond_formation
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22
US20060217346A1
CC(C)(C)OC(=O)C(Br)Oc1cc(Cl)cc(Cl)c1
C[O-]
NA
COC(Oc1cc(Cl)cc(Cl)c1)C(=O)OC(C)(C)C
# Reaction Trace ## 1. Reaction Type **Nucleophilic substitution (SN2)** — specifically, displacement of bromide from an α-halo-α-aryloxy ester by methoxide. Classified as an O-alkylation/ether synthesis (Williamson-type). ## 2. Transformation - **Bond broken:** C–Br at the α-carbon of the tert-butyl ester. - **Bond ...
Alpha-halo ester, SN2 with methoxide. Note: Br is on carbon bearing OR (aryl ether) and ester — actually structure: tert-butyl (bromo)(aryloxy)acetate. Methoxide displaces Br via SN2.
moonshotai/Kimi-K3
low
354
600
heteroatom_alkylation_arylation
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23
US09133104B2
O=[N+]([O-])c1cccc(CBr)c1
N
NA
NCc1cccc([N+](=O)[O-])c1
# Reaction Trace: 3-Nitrobenzyl Bromide → 3-Nitrobenzylamine ## 1. Reaction Type **Nucleophilic substitution (S_N2) — alkylation of ammonia.** This is the direct conversion of a primary benzylic alkyl halide to a primary amine using ammonia as the nucleophile (a variant of amine alkylation; related to the Delépine/Gab...
Benzylic bromide + ammonia → benzylamine. SN2.
moonshotai/Kimi-K3
low
332
614
fgi
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24
US20040224976A1
C[Si](C)(C)C#Cc1coc2ccc(C(=O)N[C@H]3CN4CCC3CC4)cc12
None specified
NA
C#Cc1coc2ccc(C(=O)N[C@H]3CN4CCC3CC4)cc12
1. **Reaction type:** **Alkyne desilylation / TMS deprotection**. A trimethylsilyl-protected terminal alkyne is converted into the corresponding terminal alkyne. Typical conditions include **TBAF in THF**, or **K₂CO₃ in MeOH/H₂O**. 2. **Transformation:** The **C(sp)–Si(CH₃)₃ bond is cleaved**, and a **C(sp)–H bond is ...
We need need infer desilylation TMS alkyne to terminal alkyne. Reagents unspecified likely TBAF or K2CO3/MeOH. Explain plausible conditions. Bond Si-C broken, C-H formed. No carbon skeleton change. Mechanism variants. Retrosyn terminal alkyne from TMS protected alkyne, itself Sonogashira. Mention TMS traceless protecti...
moonshotai/Kimi-K3
low
365
582
deprotections
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25
US05872117
CS(=O)(=O)Cl
CC(=O)OC(COCCO)c1cccc(Cl)c1
NA
CC(=O)OC(COCCOS(C)(=O)=O)c1cccc(Cl)c1
# Reaction Trace: Mesylation of a Primary Alcohol ## 1. Reaction Type **Mesylation (sulfonate ester formation)** — conversion of an alcohol into a methanesulfonate (mesylate) via nucleophilic substitution at sulfur. Classified as an *O-sulfonylation / alcohol activation* reaction. ## 2. Transformation - **Bonds broke...
Mesylation of terminal primary alcohol on ethylene glycol monoether; acetate untouched. Note substrate: Ar-CH(OAc)-CH2-O-CH2CH2-OH, mesylate terminal OH.
moonshotai/Kimi-K3
low
348
609
heteroatom_alkylation_arylation
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26
US20090286778A1
Clc1cnc2nc1Nc1ccc(OCCC3CCNCC3)c(c1)CCc1cncc(c1)N2
O=C=NCc1ccco1
NA
O=C(NCc1ccco1)N1CCC(CCOc2ccc3cc2CCc2cncc(c2)Nc2ncc(Cl)c(n2)N3)CC1
**1. Reaction type:** Isocyanate aminolysis / urea formation — N-carbamoylation of a secondary cyclic amine (piperidine) with furfuryl isocyanate. **2. Transformation:** The free piperidine N–H in the macrocyclic starting material adds across the isocyanate C=N bond. The key new bond is **piperidine N–C(=O)**, giving ...
The user wants a reaction trace. Let me analyze the chemistry. Starting material contains a free piperidine NH (CCNCC3 = piperidin-4-yl with NH). Reagent is furfuryl isocyanate O=C=NCc1ccco1 (2-furfuryl isocyanate). Product shows the piperidine N has been converted to N-C(=O)-NH-CH2-furyl? Wait product: O=C(NCc1ccco1)...
moonshotai/Kimi-K3
low
382
1,003
acylation
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27
US05556977
Brc1ccc(OCc2ccccc2)cc1
O=C1CN(c2ccncc2)CCN1
NA
O=C1CN(c2ccncc2)CCN1c1ccc(OCc2ccccc2)cc1
1. **Reaction type**: Palladium-catalyzed **Buchwald–Hartwig C–N cross-coupling** (N-arylation of a lactam/aza-lactam). With copper catalysis, the analogous transformation would be an Ullmann–Goldberg coupling. 2. **Transformation**: The C–Br bond of 1-bromo-4-(benzyloxy)benzene is replaced by a C–N bond. The remainin...
We need need infer reaction. Aryl bromide + lactam NH? Product N-aryl at piperazinone nitrogen. Likely Buchwald-Hartwig amination / Ullmann. No conditions specified. Need mention catalyst/base/ligand unspecified. Starting heterocycle O=C1CN(pyridyl)CCN1 has one N substituted pyridyl, other NH arylated. Mechanism oxidat...
moonshotai/Kimi-K3
low
352
582
heteroatom_alkylation_arylation
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28
US20030232832A1
CCC(O)c1nn2cccc2c(=O)n1Cc1ccccc1
CC(C)(C)OC(=O)NCCCN
NA
CCC(NCCCNC(=O)OC(C)(C)C)c1nn2cccc2c(=O)n1Cc1ccccc1
# Reaction Trace **1. Reaction Type:** Mitsunobu reaction — stereospecific substitution of a secondary alcohol with an amine nucleophile (C–O → C–N conversion). Typically employs PPh₃ and an azodicarboxylate (DEAD/DIAD), which are implied even though not listed in the reagent string. **2. Transformation:** The C–OH b...
Alcohol to amine with N-Boc-1,3-diaminopropane — likely Mitsunobu reaction.
moonshotai/Kimi-K3
low
362
528
heteroatom_alkylation_arylation
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29
US08258134B2
COC(=O)C(CC1CCCC1)n1ncc(Oc2ccccc2C(C)=O)cc1=O
None specified
NA
CC(=O)c1ccccc1Oc1cnn(C(CC2CCCC2)C(=O)O)c(=O)c1
1. **Reaction type**: Methyl ester hydrolysis / de-esterification, a functional-group interconversion converting a methyl ester to the carboxylic acid. Typically base-promoted saponification followed by acidic workup, though reagents are not specified here. 2. **Transformation**: The ester substituent `COC(=O)–` becom...
The user wants a reaction trace for conversion of methyl ester to carboxylic acid. Starting material has COC(=O) (methyl ester) and product has C(=O)OH. No reagents specified, conditions NA. This is ester hydrolysis (saponification/acidic hydrolysis), deprotection of methyl ester to carboxylic acid. Need cover items co...
moonshotai/Kimi-K3
low
362
799
deprotections
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30
US20110092461A1
O=C(O)c1ccc(-n2cncn2)nc1
Nc1ccc(Cl)c(-c2ccccn2)c1
NA
O=C(Nc1ccc(Cl)c(-c2ccccn2)c1)c1ccc(-n2cncn2)nc1
# Reaction Trace: Amide Bond Formation (Acid + Aniline Coupling) ## 1. Reaction Type **Amide coupling / condensation** — direct formation of an amide from a carboxylic acid and a primary amine. Under "NA" conditions, this would typically employ a coupling reagent (e.g., HATU, EDCI, or CDI) with a base (DIPEA/Et₃N) in ...
Amide coupling of carboxylic acid with aniline.
moonshotai/Kimi-K3
low
360
604
acylation
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31
US04298535
C=CC(C)=O
C=C1C(=C)C2OC1C(=C)C2=C
NA
C=C1C(=C)C2OC1C1=C2CC(C(C)=O)CC1
# Reaction Trace ## 1. Reaction Type **Diels–Alder [4+2] cycloaddition** — a thermal, pericyclic reaction between a conjugated diene (one of the exocyclic 1,3-diene units embedded in the 7-oxabicyclo[2.2.1]heptadiene framework) and an electron-poor dienophile (methyl vinyl ketone, MVK). ## 2. Transformation - **Bonds...
Diels-Alder: diene is 7-oxanorbornadiene-type tetrakis(methylene)? Actually diene: C=C1C(=C)C2OC1C(=C)C2=C — an oxabicyclic with exocyclic methylenes acting as diene, reacting with MVK.
moonshotai/Kimi-K3
low
349
635
heteroatom_alkylation_arylation
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32
US06051731
O=CCc1ccc(Br)cc1
CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
NA
CCOC(=O)C=CCc1ccc(Br)cc1
## Reaction Trace **1. Reaction Type** Wittig olefination — specifically, a stabilized ylide Wittig reaction (Horner-type not used here; this is the classic phosphonium ylide variant, ethyl (triphenylphosphoranylidene)acetate). **2. Transformation** - Broken: C=O π-bond of the aldehyde (O=CH–CH₂–Ar); P=C bond of the ...
Wittig reaction with stabilized ylide.
moonshotai/Kimi-K3
low
351
603
fga
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33
US20120142685A1
CC(C)(C)OC(=O)N1CCN(c2nc(-c3ccnc(Cl)c3)cc3cnccc23)CC1
NC1CCOCC1
NA
CC(C)(C)OC(=O)N1CCN(c2nc(-c3ccnc(NC4CCOCC4)c3)cc3cnccc23)CC1
**1. Reaction type:** Nucleophilic aromatic substitution (SNAr) — amination of an activated heteroaryl chloride with a secondary amine (tetrahydropyran-4-amine). **2. Transformation:** The C–Cl bond on the pyridine ring of the pendant 2-pyridyl group is broken, and a new C–N bond forms between that carbon and the amin...
SNAr on chloropyridine.
moonshotai/Kimi-K3
low
380
508
heteroatom_alkylation_arylation
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34
US08664216B2
C=O
Clc1ccc2c(c1)CNCc1nnc(Br)n1-2
NA
CN1Cc2cc(Cl)ccc2-n2c(Br)nnc2C1
# Reaction Trace **1. Reaction Type** Reductive amination / N-methylation (Eschweiler–Clarke-type methylation). A secondary amine is converted to a tertiary N-methyl amine using formaldehyde as the C1 source. **2. Transformation** - Broken: one N–H bond of the cyclic secondary amine; C=O π-bond of formaldehyde. - For...
Formaldehyde methylates secondary amine: reductive methylation? Actually formaldehyde + amine → N-methyl via iminium; but no reductant listed. Product: the secondary amine in the tetrahydro ring gets N-methyl. This is Eschweiler–Clarke-like methylation (requires formic acid) or reductive amination. Given only C=O, clas...
moonshotai/Kimi-K3
low
343
572
heteroatom_alkylation_arylation
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35
US04564609
O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1
CNC
NA
CN(C)C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1
## Reaction Trace **1. Reaction type** Amide bond formation (aminolysis) — direct coupling of a carboxylic acid with a secondary amine to give a tertiary amide. In practice this requires activation (e.g., EDCI/HOBt, HATU, or conversion to an acyl chloride/mixed anhydride), since "conditions NA" implies a standard pept...
Amidation of Cbz-proline carboxylic acid with dimethylamine. Note: conditions NA — normally requires coupling reagent; mention that.
moonshotai/Kimi-K3
low
350
556
acylation
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36
US20120016029A1
CCOC(=O)Cc1ccc(OC)c(Oc2ccc([N+](=O)[O-])cc2CBr)c1
FC(F)(F)CS
NA
CCOC(=O)Cc1ccc(OC)c(Oc2ccc([N+](=O)[O-])cc2CSCC(F)(F)F)c1
1. **Reaction type**: Nucleophilic aliphatic substitution at a primary benzylic carbon; specifically an **SN2 thioether formation / Williamson-type thioether synthesis**. Benzyl bromide → benzyl 2,2,2-trifluoroethyl sulfide. 2. **Transformation**: The benzylic **C–Br bond** is broken and a new **benzylic C–S bond** is...
We need answer with trace. Need craft accurate chemistry. Let's reason. Starting material: ethyl 2-(4-methoxy-3-(4-nitro-2-(bromomethyl)phenoxy)phenyl)acetate? It has benzyl bromide aryl-CH2Br ortho to diaryl ether and para? Reagent FC(F)(F)CS = HSCH2CF3? Actually SMILES FC(F)(F)CS: 2,2,2-trifluoroethanethiol (CF3CH2S...
moonshotai/Kimi-K3
low
374
913
heteroatom_alkylation_arylation
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37
US07964613B2
O=S(=O)(Cl)c1cccc2cncc(Cl)c12
CC(C)(C)OC(=O)NCC1CCNCC1
NA
CC(C)(C)OC(=O)NCC1CCN(S(=O)(=O)c2cccc3cncc(Cl)c23)CC1
1. **Reaction type:** **N-Sulfonylation (sulfonamide formation)**. A secondary piperidine nitrogen displaces chloride from an aryl sulfonyl chloride to form an arylsulfonamide. This is nucleophilic substitution at sulfur, not displacement of the heteroaryl C–Cl bond. 2. **Transformation:** - **Broken:** the S–Cl ...
We need craft 150-300. Need mention sulfonamide formation, likely base needed though absent, Boc carbamate intact. Cl aryl unaffected. Mechanism nucleophilic substitution at sulfur, HCl scavenger. Carbon skeleton attached. Retrosynth disconnect N-S.
moonshotai/Kimi-K3
low
368
551
acylation
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38
US20090081165A1
CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1
N[C@H]1CC[C@H](O)CC1
NA
CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c([N+](=O)[O-])c1
## Reaction Trace **1. Reaction type:** Nucleophilic aromatic substitution (S_NAr) — an addition–elimination substitution of an aryl chloride by an amine nucleophile. **2. Transformation:** The C(sp²)–Cl bond at the position para to the nitro group is broken, and a new C(sp²)–N bond is formed between the aryl carbon ...
SNAr, nitro-activated aryl chloride, amine displaces Cl.
moonshotai/Kimi-K3
low
373
499
heteroatom_alkylation_arylation
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39
US08404673B2
CC(=O)N1CCC(=O)CC1
COc1cc(C(F)(F)F)cc(C(F)(F)F)c1C(=O)N[C@@H]1CCCC[C@@H]1N
NA
COc1cc(C(F)(F)F)cc(C(F)(F)F)c1C(=O)N[C@@H]1CCCC[C@@H]1NC1CCN(C(C)=O)CC1
1. **Reaction type:** **Reductive amination** of a ketone with a primary amine. It is a C–N bond-forming reductive coupling. 2. **Transformation:** The ketone carbonyl in **N-acetyl-4-piperidone** is converted into a C–N bond to the free primary amine of the trans-cyclohexanediamine derivative. The π bond of **C4...
We need need note missing reducing agent. Conditions NA, inferred reductive amination. Ketone plus primary diamine terminal NH2. Mechanism imine then reduction. Bond broken C=O pi, N-H perhaps; formed C-N, C-H and likely N-H changes. Reagent roles starting amine, ketone; hydride source not listed. Could maybe direct re...
moonshotai/Kimi-K3
low
399
681
heteroatom_alkylation_arylation
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40
US06888000B2
O=S(=O)(Cl)c1ccccc1
CCCCCc1nc2c(N)nc3ccccc3c2n1CCCCN
NA
CCCCCc1nc2c(N)nc3ccccc3c2n1CCCCNS(=O)(=O)c1ccccc1
1. **Reaction type**: **N-sulfonylation** of a primary aliphatic amine with an arenesulfonyl chloride; specifically a **Schotten–Baumann-type sulfonamide formation**. Classified as nucleophilic substitution at sulfur(VI), not carbon substitution. 2. **Transformation**: The terminal **–CH2CH2CH2CH2NH2** side chain is c...
The user wants a reaction trace. Need identify chemistry: benzenesulfonyl chloride reacts with terminal primary amine on imidazoquinoline-like alkyl chain to sulfonamide. Product has N-sulfonylation of butylamine substituent: R-NH2 + PhSO2Cl -> R-NHSO2Ph + HCl. Conditions NA likely base (Et3N/pyridine) implied, Schotte...
moonshotai/Kimi-K3
low
362
868
acylation
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41
US07285558B2
CC(C)Cn1c(=O)n(C)c(=O)c2c(-c3cc(C(=O)O)cn3C)n(Cc3c[nH]c4ccc(Cl)cc34)nc21
CC(C)NCCN
NA
CC(C)Cn1c(=O)n(C)c(=O)c2c(-c3cc(C(=O)NCCNC(C)C)cn3C)n(Cc3c[nH]c4ccc(Cl)cc34)nc21
# Reaction Trace: Amide Bond Formation (Carboxylic Acid + Primary Amine) ## 1. Reaction Type **Amide coupling (aminolysis of a carboxylic acid)** — a nucleophilic acyl substitution converting the pyrrole-2-carboxylic acid into an N-substituted carboxamide using *N*-isopropylethylenediamine. ## 2. Transformation - **B...
Carboxylic acid → amide with N-isopropylethylenediamine.
moonshotai/Kimi-K3
low
412
578
acylation
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42
US04006232
ClCCCN1CCN(c2ccccc2)CC1
O=C1NC(=O)C(c2ccccc2)(c2ccccc2)N1
NA
O=C1NC(c2ccccc2)(c2ccccc2)C(=O)N1CCCN1CCN(c2ccccc2)CC1
### 1. Reaction type **N-Alkylation of a hydantoin via an SN2 substitution.** The nucleophilic nitrogen of 5,5-diphenylhydantoin displaces chloride from 1-(3-chloropropyl)-4-phenylpiperazine. ### 2. Transformation - **Bond broken:** terminal **C–Cl** bond of the three-carbon alkyl chloride. - **Bond formed:** **N–CH2*...
We need identify N-alkylation hydantoin by 3-chloropropyl piperazine. Need nuanced which N? Starting hydantoin 5,5-diphenyl? SMILES O=C1NC(=O)C...N1. Product one N alkylated. SN2, base likely omitted. Explain deprotonation imide N, substitution chloride. Hydantoin has two N, tautomer/regioselectivity perhaps N-alkylati...
moonshotai/Kimi-K3
low
372
652
heteroatom_alkylation_arylation
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43
US04927956
CC(=O)Cl
Cc1ccccc1O
NA
CC(=O)Oc1ccccc1C
# Reaction Trace: Acetylation of o-Cresol ## 1. Reaction Type **Nucleophilic acyl substitution — esterification via acid chloride** (alcohol acylation; Schotten–Baumann type ester formation). This is the conversion of a phenol into a phenyl ester using an acyl chloride. ## 2. Transformation - **Bond broken:** C–Cl bo...
Acetyl chloride + o-cresol → aryl acetate (Fischer esterification via acid chloride / Schotten-Baumann acylation).
moonshotai/Kimi-K3
low
322
616
protections
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44
US20100009970A1
CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
CN[C@H]1CC[C@@H](c2ccc(Cl)c(Cl)c2)c2ccc(C(=O)OC)cc21
NA
COC(=O)c1ccc2c(c1)[C@@H](N(C)C(=O)OC(C)(C)C)CC[C@H]2c1ccc(Cl)c(Cl)c1
# Reaction Trace: N-Boc Protection of a Secondary Amine ## 1. Reaction Type **N-Boc protection (carbamate formation)** — a protecting group installation. Specifically, acylation of a secondary amine with di-tert-butyl dicarbonate (Boc₂O) to form a tert-butyl carbamate. ## 2. Transformation - **Bonds formed**: N–C(=O)...
Boc protection of secondary amine with Boc2O.
moonshotai/Kimi-K3
low
401
641
protections
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45
US06153768
Cc1ccc(S(=O)(=O)Cl)cc1
COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCO)cc1
NA
COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCOS(=O)(=O)c2ccc(C)cc2)cc1
## Reaction Trace **1. Reaction type** O-Tosylation (sulfonate ester formation) — conversion of a primary alcohol into a p-toluenesulfonate (tosylate) ester using tosyl chloride (TsCl). Classified as nucleophilic substitution at sulfur (functional group interconversion, protecting/activating group installation). **2....
Tosylation of primary alcohol.
moonshotai/Kimi-K3
low
381
584
protections
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46
US20090105305A1
Cc1ccc(C(=O)N2CCC(c3ccc(C#N)cc3)CC2)cc1NS(=O)(=O)c1cccc(C(=O)O)c1
CNC
NA
Cc1ccc(C(=O)N2CCC(c3ccc(C#N)cc3)CC2)cc1NS(=O)(=O)c1cccc(C(=O)N(C)C)c1
1. **Reaction type**: Carboxylic acid → tertiary amide formation; an **aminocarbonylation/amidation** of a benzoic acid with dimethylamine. Classified as nucleophilic acyl substitution at a carboxyl carbon. 2. **Transformation**: The meta-benzoic acid group on the sulfonyl aryl ring, `Ar–C(=O)OH`, is converted to `Ar–...
The user wants a reaction trace for conversion of benzoic acid to dimethylamide using dimethylamine (CNC). This is a standard amidation (carboxylic acid + amine -> amide). Need mention activation/coupling reagent implied though NA; direct thermal aminolysis unlikely. We should say likely peptide-coupling conditions (e....
moonshotai/Kimi-K3
low
391
746
deprotections
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47
US20150018332A1
Ic1c[nH]cn1
OB(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1
NA
FC(F)(F)c1cc(-c2c[nH]cn2)cc(C(F)(F)F)c1
1. **Reaction type** **Suzuki–Miyaura cross-coupling**: a palladium-catalyzed coupling of an aryl iodide with an arylboronic acid. 2. **Transformation** The imidazole–carbon–iodine bond is cleaved, and the B–C bond of 3,5-bis(trifluoromethyl)phenylboronic acid is functionalized. A new **C(sp²)–C(sp²) bond** ...
We need note missing Pd/base conditions. It is Suzuki-Miyaura. Aryl boronic acid + 4(?) iodoimidazole. Product positions. Mechanism standard. Conditions NA cannot infer but typically Pd catalyst/base. Reagent role starting organohalide substrate and boronic acid. Need perhaps iodide at C4.
moonshotai/Kimi-K3
low
355
598
cc_bond_formation
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48
US05654299
O=C(Cl)OCc1ccccc1
N#CC1CCNCC1
NA
N#CC1CCN(C(=O)OCc2ccccc2)CC1
# Reaction Trace: N-Cbz Protection of 4-Cyanopiperidine ## 1. Reaction Type **Nucleophilic acyl substitution (N-protection)** — specifically, installation of a benzyloxycarbonyl (Cbz/Z) protecting group onto a secondary amine using benzyl chloroformate (Cbz-Cl). ## 2. Transformation - **Bond broken:** C–Cl of the chl...
Reaction: benzyl chloroformate + 4-cyanopiperidine → N-Cbz protection.
moonshotai/Kimi-K3
low
338
569
acylation
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49
US20120101079A1
CCSc1nc(Cl)cc(C)c1C(=O)NCc1cccc(F)c1
OC[C@H]1COCCN1
NA
CCSc1nc(N2CCOC[C@@H]2CO)cc(C)c1C(=O)NCc1cccc(F)c1
# Reaction Trace: Nucleophilic Aromatic Substitution (S_NAr) on a Chloropyrimidine ## 1. Reaction Type **Nucleophilic aromatic substitution (S_NAr)** of a heteroaryl chloride with a secondary amine — specifically, amination of 2-chloropyrimidine with (3R)-3-(hydroxymethyl)morpholine. ## 2. Transformation - **Bond bro...
SNAr on chloropyrimidine with morpholine amine.
moonshotai/Kimi-K3
low
363
617
heteroatom_alkylation_arylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
50
US20120095249A1
CC1(C)[C@@]2(C)CC[C@]1(C(=O)Nc1ccc(Cl)cc1C(=O)C(F)(F)F)OC2=O
C#CC1CC1
NA
CC1(C)[C@@]2(C)CC[C@]1(C(=O)Nc1ccc(Cl)cc1[C@@](O)(C#CC1CC1)C(F)(F)F)OC2=O
**1. Reaction type** Nucleophilic addition of a terminal alkyne to a carbonyl — specifically, alkynylation of an α,α,α-trifluoromethyl ketone to give a tertiary propargylic alcohol (ethynylcyclopropane addition; typically mediated by deprotonation with a strong base such as n-BuLi or an organozinc/halo-magnesium acetyl...
Addition of alkynyl anion to trifluoromethyl ketone.
moonshotai/Kimi-K3
low
400
585
cc_bond_formation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
51
US06492393B1
Cc1ccc(C(C)(C)C)cc1[N+](=O)[O-]
None specified
NA
Cc1ccc(C(C)(C)C)cc1N
## Reaction Trace ### 1. Reaction Type **Nitro group reduction (reduction of an aromatic nitro compound to a primary amine)** — a redox transformation converting Ar–NO₂ → Ar–NH₂. Classic methods: catalytic hydrogenation (H₂/Pd-C, PtO₂, or Raney Ni) or dissolving-metal reduction (Fe, Zn, or Sn with HCl; or SnCl₂/HCl). ...
Nitro reduction to aniline.
moonshotai/Kimi-K3
low
334
602
reductions
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
52
US20140235623A1
CNc1cccc(N)c1C#N
O=C=NC(=O)c1ccccc1
NA
CNc1cccc(NC(=O)NC(=O)c2ccccc2)c1C#N
1. **Reaction type**: Nucleophilic addition of an aniline to an **acyl isocyanate** to form an **N-acyl urea**; specifically urea formation via amine–isocyanate coupling. No metal catalysis; classified as aza-addition/condensation without loss of a leaving group. 2. **Transformation**: The free aniline –NH2 of CNc1ccc...
Isocyanate O=C=NC(=O)c1ccccc1 = benzoyl isocyanate (benzoylcarbonyl isocyanate): Ph-C(=O)-N=C=O, an acyl isocyanate. The free aniline attacks isocyanate carbon to form urea: ArNH-C(=O)-NH-C(=O)Ph. Product shows Ar-NC(=O)NC(=O)c2ccccc2 (N-benzoyl-N'-aryl urea). N-methyl and nitrile untouched. Need 150-300 words concise...
moonshotai/Kimi-K3
low
345
1,037
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
53
US20110207731A1
O=S(=O)(Cl)Cc1ccc(F)cc1
CC1=C(C#N)C(c2ccc3c(c2)c(N)nn3C(=O)OC(C)(C)C)C(C#N)=C(C)N1
NA
CC1=C(C#N)C(c2ccc3c(c2)c(NS(=O)(=O)Cc2ccc(F)cc2)nn3C(=O)OC(C)(C)C)C(C#N)=C(C)N1
### 1. Reaction type **N-Sulfonylation (sulfonamide formation).** A nucleophilic exocyclic amine reacts with **(4-fluorophenyl)methanesulfonyl chloride** to form an arylmethyl sulfonamide. ### 2. Transformation - **Broken:** amine N–H bond and sulfonyl S–Cl bond. - **Formed:** new **N–S bond** between the pyrazole-der...
We need need formulate. Reaction sulfonylation amine with sulfonyl chloride. Starting "reagent" is complex DHP amine likely substrate, sulfonyl chloride. No base listed but amine perhaps sacrificial/pyridine-like dihydropyridine and likely standard. Need not overstate. Product sulfonamide N-H. Bonds N-H and S-Cl broken...
moonshotai/Kimi-K3
low
412
707
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
54
US20090054398A1
O=C(Cc1cc(F)cc(F)c1)N[C@@H](Cc1cc2ccccc2[nH]1)C(=O)O
N[C@H]1C(=O)Nc2ccccc2S[C@H]1c1ccccc1
NA
O=C(Cc1cc(F)cc(F)c1)N[C@@H](Cc1cc2ccccc2[nH]1)C(=O)N[C@@H]1C(=O)Nc2ccccc2S[C@@H]1c1ccccc1
### 1. Reaction type **Amide-bond formation (peptide coupling)** between a carboxylic acid and a primary amine. The reaction is formally dehydrative. ### 2. Transformation - **Broken:** the carboxylic acid **C(=O)–OH** bond of the N-acyl tryptophan derivative; an **N–H** bond of the primary amine reagent. - **Formed:*...
We need answer needs notice ambiguity reagent is amino lactam, product coupling with carboxylic acid, peptide bond. Conditions NA, unspecified coupling reagent likely direct amide formation. Also stereochem: amine SMILES N[C@H]1 and S[C@H], product N[C@@H] and S[C@@H], potentially SMILES representation changes due prio...
moonshotai/Kimi-K3
low
424
751
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
55
US20140309193A1
CCOC(=O)c1c(OCc2ccccc2)c(OCc2ccccc2)c(C(=O)N(C)C)n1-c1ccc(OC)cc1
CCN
NA
CCNC(=O)c1c(OCc2ccccc2)c(OCc2ccccc2)c(C(=O)N(C)C)n1-c1ccc(OC)cc1
# Reaction Trace **1. Reaction Type** Aminolysis of an ester — a nucleophilic acyl substitution converting an ethyl ester into an N-ethyl amide using ethylamine (CCN). **2. Transformation** The bond broken is the acyl C–O bond of the ethyl ester [C(=O)–OEt]; the bond formed is the new C–N bond to ethylamine [C(=O)–NH...
Ester aminolysis: ethyl ester → N-ethyl amide via ethylamine.
moonshotai/Kimi-K3
low
387
541
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
56
US20080221096A1
CN(Cc1ccccc1)c1nc2oc3c(Cl)ncnc3c2c2c1COC(C)(C)C2
NCCN1CCOCC1
NA
CN(Cc1ccccc1)c1nc2oc3c(NCCN4CCOCC4)ncnc3c2c2c1COC(C)(C)C2
### 1. Reaction type **Nucleophilic aromatic substitution (SNAr)** on an electron-poor, fused heteroaromatic chloride; specifically, an **amination of a chloroazaarene**. The primary amine of \( \mathrm{H_2NCH_2CH_2N} \)-morpholine displaces chloride. ### 2. Transformation The aryl/heteroaryl **C–Cl bond is broken**, ...
We need craft 150-300. Need inspect structure: substitution Cl by amine on fused pyrimidine? SNAr. Product replaces Cl with NHCH2CH2N-morpholine. Reagent H2N-CH2CH2-N(morpholine), diamine nucleophile. Conditions NA maybe neat/heat, base not specified. Mechanism addition-elimination. Need mention NH remains. Could ambig...
moonshotai/Kimi-K3
low
381
615
heteroatom_alkylation_arylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
57
US07820704B2
Clc1nccc(NC2CCCC2)n1
OB(O)c1ccc(OCc2ccccc2)cc1
NA
c1ccc(COc2ccc(-c3nccc(NC4CCCC4)n3)cc2)cc1
# Reaction Trace: Suzuki–Miyaura Cross-Coupling ## 1. Reaction Type **Suzuki–Miyaura cross-coupling** — a palladium-catalyzed C(sp²)–C(sp²) bond formation between an aryl (heteroaryl) halide and an arylboronic acid. ## 2. Transformation - **Broken:** The C2–Cl bond of 2-chloro-*N*-cyclopentylpyrimidin-4-amine; the C–...
This is a Suzuki-Miyaura coupling: 2-chloro pyrimidine + arylboronic acid → biaryl. Conditions NA but typical Pd catalyst/base.
moonshotai/Kimi-K3
low
351
631
cc_bond_formation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
58
US20090221555A1
C#CCNC(=O)c1cccc(F)c1Nc1nc(Cl)ncc1Cl
CCN1CC(O)(CO)COc2cc(N)ccc21
NA
C#CCNC(=O)c1cccc(F)c1Nc1nc(Nc2ccc3c(c2)OCC(O)(CO)CN3CC)ncc1Cl
### 1. Reaction type **Nucleophilic aromatic substitution (SNAr), specifically heteroaryl chloro–amine displacement (amination)** of a polychlorinated nitrogen heterocycle. No transition-metal-catalyzed coupling is involved. ### 2. Transformation - **Broken:** the aryl/heteroaryl **C–Cl bond** at the more activated ch...
We need craft. Need identify SNAr aminolysis on chloropyrimidine. Starting heteroaryl chloride Nc1nc(Cl)ncc1Cl, aniline/benzomorpholine amine attacks 2-Cl? Product Cl remains at other position, replacing Cl by Nc2... Need clarify bonds. Mechanism addition elimination, amine attacks activated carbon bearing Cl, Meisenh...
moonshotai/Kimi-K3
low
375
656
heteroatom_alkylation_arylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
59
US08003677B2
O=C(O)c1ccc(N2CC3=C(CN(C(=O)c4ccccc4C(F)(F)F)C3)C2)nc1
NCCC1CC1
NA
O=C(NCCC1CC1)c1ccc(N2CC3=C(CN(C(=O)c4ccccc4C(F)(F)F)C3)C2)nc1
# Reaction Trace: Carboxylic Acid → Amide Coupling ## 1. Reaction Type **Amide bond formation (aminolysis / coupling of a carboxylic acid with a primary amine)** — a condensation reaction converting a benzoic acid derivative into a secondary amide. In practice this would proceed via activation of the acid (e.g., acid ...
Amidation of carboxylic acid with primary amine.
moonshotai/Kimi-K3
low
382
616
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
60
US20130143892A1
N#Cc1ccc(-c2cc(C(=O)O)on2)c(F)c1
CC(C)(C)c1noc(N2CCC(NC3CC3)CC2)n1
NA
CC(C)(C)c1noc(N2CCC(N(C(=O)c3cc(-c4ccc(C#N)cc4F)no3)C3CC3)CC2)n1
1. **Reaction type**: **Amide-bond formation / nucleophilic acyl substitution**, i.e. peptide-style coupling of a heteroaryl carboxylic acid with a secondary amine to give a **tertiary amide**. Aryl–F, nitrile, isoxazole, and tert-butyl-oxadiazole groups are spectators. 2. **Transformation**: The carboxylic acid **C(=...
We need answer user asks reaction trace. Need infer chemistry. Need formulate concise 150-300 words. Need analyze reaction. We have starting material: N#Cc1ccc(-c2cc(C(=O)O)on2)c(F)c1. This is a benzonitrile ortho F attached to isoxazole? Let's parse: N#Cc1ccc(-c2cc(C(=O)O)on2)c(F)c1. Aryl nitrile with F ortho to isox...
moonshotai/Kimi-K3
low
383
1,320
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
61
US20090123563A1
O=C1CCC(=O)N1Br
Cc1ccc(C(=O)O)cc1F
NA
O=C(O)c1ccc(CBr)c(F)c1
## Reaction Trace: Benzylic Bromination with NBS **1. Reaction type** Free-radical benzylic bromination (Wohl–Ziegler-type) using N-bromosuccinimide (NBS). **2. Transformation** The starting material, 2-fluoro-4-methylbenzoic acid (SMILES: Cc1ccc(C(=O)O)cc1F), has a benzylic C–H bond on the ring methyl group. This C–...
NBS benzylic bromination.
moonshotai/Kimi-K3
low
335
580
fgi
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
62
US20090105305A1
COC(=O)CS(=O)(=O)Nc1cc(C(=O)N2CCC(c3ccc(C#N)cc3)CC2)ccc1C
None specified
NA
Cc1ccc(C(=O)N2CCC(c3ccc(C#N)cc3)CC2)cc1NS(=O)(=O)CC(=O)O
# Reaction Trace: Methyl Ester Hydrolysis (Saponification) ## 1. Reaction Type **Ester hydrolysis** (saponification / base- or acid-catalyzed ester cleavage) — a deprotection/hydrolysis reaction. The methyl ester of an α-sulfonyl acetic acid is converted to the free carboxylic acid. ## 2. Transformation - **Bonds bro...
Ester hydrolysis methyl ester to carboxylic acid.
moonshotai/Kimi-K3
low
382
660
deprotections
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
63
US07910592B2
O=S(=O)(OC1=CCC2(CC1)OCCO2)C(F)(F)F
COc1ccc(B(O)O)cc1
NA
COc1ccc(C2=CCC3(CC2)OCCO3)cc1
1. **Reaction type** **Suzuki–Miyaura cross-coupling**: a palladium-catalyzed coupling of an **alkenyl triflate** with an **arylboronic acid**. A Pd(0) catalyst, base, and suitable solvent are required even though they are not specified. 2. **Transformation** The **C(sp²)–O(triflate)** bond of the cyclohexen...
We need need formulate. Reaction vinyl triflate + aryl boronic acid Suzuki, but missing base/Pd in stated. Mention required inferred. Product stereochem? cyclic alkene and spiro ketal preserved. Need mechanism steps.
moonshotai/Kimi-K3
low
356
587
cc_bond_formation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
64
US20070066624A1
CC(C)(C)OC(=O)N1CCC(N2C(=O)NC[C@H]2c2ccccc2)CC1
CN=C=O
NA
CNC(=O)N1C[C@@H](c2ccccc2)N(C2CCN(C(=O)OC(C)(C)C)CC2)C1=O
1. **Reaction type** **N-Carbamoylation of a cyclic urea with an isocyanate**. Methyl isocyanate converts the imidazolidin-2-one N–H into an **N-(methylcarbamoyl)** substituent, forming a biuret-like linkage. 2. **Transformation** - Broken: the cyclic urea **N–H bond** and one π component of the isocyanate *...
We need need identify N-methylation via isocyanate addition to cyclic urea NH. Starting has imidazolidin-2-one NH; methyl isocyanate gives N-methylcarboxamide substituent, actually product CNC(=O)N1... meaning N-carbamoylation: ring urea N adds to isocyanate carbon, yielding N-(methylcarbamoyl) imidazolidinone (biuret-...
moonshotai/Kimi-K3
low
379
671
acylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
65
US07598393B2
O=[N+]([O-])c1cc(Br)ccc1Br
NCC1(O)CCCC1
NA
O=[N+]([O-])c1cc(Br)ccc1NCC1(O)CCCC1
**Reaction Trace: SNAr of 1-(1-Hydroxycyclopentyl)methylamine with a Nitroaryl Bromide** 1. **Reaction type**: Nucleophilic aromatic substitution (SNAr) — amination of an activated aryl halide. Classified as a C–N bond-forming substitution. 2. **Transformation**: The C–Br bond *ortho* to the nitro group is broken, an...
Nucleophilic aromatic substitution of aryl bromide by amine, ortho/para to nitro. Starting: 1,2-dibromo-4-nitrobenzene? Br displaced at position adjacent to nitro.
moonshotai/Kimi-K3
low
348
545
heteroatom_alkylation_arylation
{"SYSTEM_PROMPT": {"len": 319, "sha256_16": "535cfdb84475881d"}, "USER_TEMPLATE": {"len": 695, "sha256_16": "c543cca7ceea341d"}}
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Resonance

Data for the preprint Distillation, Self-Training, and the Fragility of Learned Chemical Reasoning (Aneesh, Ibarraran, Hu, Liu, Rotskoff, 2026).

Resonance trains open-weight models to predict the product of a chemical reaction from its SMILES, reasoning step by step. A teacher (Kimi K3) writes a reasoning trace for every USPTO-50k training reaction. The student (Qwen3-8B or Qwen3.8-27B) is fine-tuned on those traces (S1), then on its own verified-correct answers (S2, rejection-sampling SFT), then on preference pairs from its own correct and incorrect answers (S3, DPO + NLL). This repository holds every dataset of that pipeline, every model's test-set outputs, and the samples behind the paper's reasoning analysis.

Everything for this paper sits under v1/; later releases will add v2/, ... alongside it. The git tag v1 fixes this version.

Configs

Config Rows Contents
v1_uspto50k 40,000 / 5,000 / 5,000 USPTO-50k train / validation / test: patent id, starting material (first reactant), reagents (other reactants), product.
v1_reaction_classes 40,000 + 5,000 Rule-based reaction class per reaction, as first published (class_published) and with the benzyl-ether correction used in the paper (class).
v1_kimi_k3_traces 40,000 S1 training data: the Kimi K3 trace for every training reaction (trace, the text the students are trained on; reasoning, the teacher's hidden reasoning field). The teacher saw the product; no reaction ids were in the prompt.
v1_s2_8b 47,492 Resonance-8B S2 training set: exactly correct S1 samples (≤ 1,024 tokens) as chat-formatted text.
v1_s2_27b 98,731 Resonance-27B S2 training set (difficulty mix, including 1,108 answer-only gold fallbacks): prompt and completion decoded from the training token ids.
v1_s3_pairs_8b 28,747 Resonance-8B S3 DPO pairs: prompt, chosen (a correct S2 sample), rejected (the most Tanimoto-similar incorrect one).
v1_s3_pairs_27b 12,079 Resonance-27B S3 DPO pairs, decoded from token ids.
v1_skip_s2_pairs_8b 26,661 Skip-S2 ablation pairs, sampled from 8B S1.
v1_skip_s2_pairs_27b 13,698 Skip-S2 ablation pairs, sampled from 27B S1.
v1_test_predictions 5,000 per model Full responses on the USPTO-50k test set for every model in the paper: both students at every stage and skip-S2, both base models, the zero-shot references (Kimi K3, Claude Opus 5, GPT-6-Astra) and the 0/4/8-shot control on base Qwen3-8B. answer is the last <answer> block, prediction its canonical SMILES, correct the paper's Top-1 exact match.
v1_reasoning_probes 27 stage × condition groups × 5,000 reactions Resonance-8B S1–S3 samples behind the reasoning analysis: fresh resamples, the reasoning-length prompts and the feedback conditions, 8 draws per reaction (responses), with per-reaction seeds.
from datasets import load_dataset

traces = load_dataset("anaghaa/resonance", "v1_kimi_k3_traces", split="train")
preds = load_dataset("anaghaa/resonance", "v1_test_predictions", split="test")
s3 = preds.filter(lambda r: r["model"] == "Resonance-8B-S3")
print(sum(s3["correct"]) / len(s3))   # 0.428

Raw files and reproducing the paper

v1/raw/<run_dir key>/<path> holds the original files at the paths the runs wrote them, laid out for the code's resonance.paths.run_dir. The code repository fetches them:

python -m resonance.download figures   # the 63 inputs of every figure (4.3 GB)
python -m resonance.download all       # plus the USPTO split and every training set (S1, S2, DPO pairs)
python -m resonance.paper.run_all --out paper_out   # rebuilds Figs 2-7, A1, A2 on a CPU

The rebuilt figures are pixel-identical to the paper's.

Scoring

A prediction is the last <answer> block anywhere in the response. It is correct if its RDKit canonical SMILES equals that of the recorded product; invalid, missing and truncated answers count as wrong (N = 5,000). Reaction classes in the paper use the corrected labels (class).

Notes

  • The reaction classes come from a rule-based classifier, not expert annotation.
  • The teacher traces were written with the product visible, and some contain chemical errors; they are released as the students saw them.
  • The Claude Opus 5 and GPT-6-Astra responses are zero-shot evaluation outputs, included so the paper's comparisons can be checked.
  • USPTO-50k is derived from US patent data (Lowe 2012; Schneider et al. 2016).

Citation

@misc{aneesh2026resonance,
  title  = {Distillation, Self-Training, and the Fragility of Learned Chemical Reasoning},
  author = {Aneesh, Anagha and Ibarraran, Sebastian and Hu, Frank and Liu, Jason and Rotskoff, Grant},
  year   = {2026},
  note   = {Preprint}
}
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