Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][CH:2]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])=[C:6]([O:29]COC)[CH:5]=1)[CH3:3].FC(F)(F)C(O)=O.O>C(Cl)Cl>[NH2:1][CH:2]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])=[C:6]([OH:29])[CH:5]=1)[CH3:3]
Reactant: COCOc1cc(C(C)N)ccc1C(=O)Nc1ccccc1C(=O)Nc1ccc(Cl)cn1
Solvent: O
Solvent: ClCCl
Solvent: O=C(O)C(F)(F)F
Product: CC(N)c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)c(O)c1
Temperature: 25 °C
Reaction time: 0.42 h
Yield: 97.4 %

Procedure:
To a solution of 2-[4-(1-aminoethyl)-2-(methoxymethoxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (0.205 g, 0.45 mmol) in CH2Cl2 (4.1 mL) was added trifluoroacetic acid (4.1 mL) followed by H2O (4.1 mL). The reaction was stirred at room temperature for 20-30 min. Then the volatile solvent was removed under a reduced pressure and the residue was diluted with H2O (20 mL) and carefully neutralized with solid NaHCO3. The aqueous solution was extracted with EtOAc (5×25 mL), dried (Na2 SO4) and concentrated to afford the expected product (0.180 g, 97%), TLC Rf: 0.36 (5% 2 N NH3/MeOH in CH2Cl2). 1H NMR (400 MHz, CD3OD): δ 8.44 (d, 1H, J=8.0 Hz); 8.31 (d, 1H, J=2.4 Hz); 8.23 (d, 1H, J=8.8 Hz); 7.93 (d, 1H, J=8.8 Hz); 7.86-7.82 (m, 2H); 7.59 (dt, 1H, J=2.0 and 8.8 Hz); 7.29 (dt, 1H, J=0.8 and 7.6 Hz); 7.00 (m, 2H); 4.39 (q, 1H, J=7.2 Hz); 1.58 (d, 3H, J=6.8 Hz). IS-MS (m/e): 411 (m+1) and 409 (m−1) H. Wang's Resin-linked 2-[4-(1-aminoethyl)-2-hydroxybenzoylamino]-N-(5-chloro-pyridin-2-yl)benzamide
Reaction SMILES: [Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[OH:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:29](OC=C)[CH3:30]>>[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[O:28][CH:29]=[CH2:30])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
Reactant: CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C1
Reactant: C=COCC
Product: C=CO[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
Temperature: 25 °C
Reaction time: 24 h

Procedure:
To a solution of 4 g of 3β-(t-butyldimethylsilyloxy)androst-5-en-17β-ol in 50 ml of vinyl ethyl ether, there was added 0.25 g of mercuric acetate. The mixture was stirred at room temperature for 24 hours, quenched with triethylamine, and then poured into dilute aqueous potassium carbonate solution. The aqueous mixture was extracted 3 times with 100 ml-portions of diethyl ether and the combined organic extracts were washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was then removed under reduced pressure and the residue was purified by flash chromatography using ethyl acetate/hexane, 1:4, to give 3β-(t-butyldimethylsilyloxy)-17β-ethenyloxyandrost-5-ene.
Reaction SMILES: [NH2:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[C:8]([I:14])=[C:7]([CH3:15])[C:3]=1[C:4]([OH:6])=O.[C:16](Cl)(=[O:20])[CH:17]([CH3:19])[CH3:18].[N:22]1C=CC=CC=1.C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.CN(C)C=O.C1C=CC=CC=1>[F:13][C:9]1[C:10]([O:11][CH3:12])=[C:2]([NH:1][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[C:3]([C:4]([NH2:22])=[O:6])=[C:7]([CH3:15])[C:8]=1[I:14]
Reactant: CC(C)C(=O)Cl
Reactant: c1ccncc1
Reactant: COc1c(N)c(C(=O)O)c(C)c(I)c1F
Agent: CC(=O)[O-]
Agent: [NH4+]
Solvent: c1ccccc1
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Product: COc1c(F)c(I)c(C)c(C(N)=O)c1NC(=O)C(C)C
Temperature: 0 °C
Reaction time: 3 h
Yield: 29.3 %

Procedure:
A benzene (10 ml) suspension of 2-amino-4-fluoro-5-iodo-3-methoxy-6-methylbenzoic acid (I-33) (500 mg, 1.54 mmol) was cooled at 0° C., isobutyryl chloride (403 μl, 3.85 mmol), pyridine (311 μl, 3.85 mmol) were put into it, followed by stirring at room temperature for 3 hours. Ethyl acetate (50 ml) was added to the reaction liquid, the organic layer was washed with 1 N hydrochloric acid (50 ml×2), saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. N,N-Dimethylformamide (5.0 ml), ammonium acetate (593 mg, 7.69 mmol) were added to the residue, followed by stirring at room temperature for 10 minutes, then stirring at 50° C. for 45 minutes. Ethyl acetate (100 ml) was added to the reaction liquid, the organic layer was washed with saturated brine (50 ml×3), dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified twice by silica gel column chromatography (chloroform:methanol=100:1→100:7), (n-hexane:ethyl acetate=3:2→chloroform:methanol=50:1) to obtain the entitled compound (178 mg, 29%) as a colorless solid.
Reaction SMILES: C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]([C@H:15]([OH:17])[CH3:16])[C:11]([O:13][CH3:14])=[O:12].Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.C(OCC)C>ClCCl>[CH3:16][C@H:15]1[O:17][C:19](=[O:21])[NH:9][C@@H:10]1[C:11]([O:13][CH3:14])=[O:12]
Reactant: O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
Reactant: COC(=O)[C@@H](N)[C@@H](C)O
Agent: Cl
Solvent: CCOCC
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: COC(=O)[C@H]1NC(=O)O[C@@H]1C
Temperature: 25 °C
Reaction time: 0.25 h

Procedure:
Triethylamine (7.40 mL, 53.1 mmol) was added slowly to a mixture of (2S,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride (3.0 g, 17.7 mmol) in dichloromethane (41 mL) at 0° C. The mixture was stirred for 15 minutes. A mixture of triphosgene (1.79 g, 6.01 mmol) in dichloromethane (15 mL) was added drop wise via addition funnel. The mixture was allowed to warm to room temperature for 14 hours. Diethyl ether (20 mL) was added, and the mixture was cooled to −78° C. for 15 minutes. The solids were filtered and the filtrate was concentrated under reduced pressure to about 10 mL. The mixture was then added to a plug of silica gel and washed slowly with ethyl acetate (˜75 mL). The filtrate was then concentrated under reduced pressure and dried under vacuum to afford (4S,5R)-methyl 5-methyl-2-oxooxazolidine-4-carboxylate. 1H NMR (500 MHz, CDCl3) δ 5.96 (s, 1H), 4.77-4.71 (m, 1H), 3.99 (d, J=5.4 Hz, 1H), 3.81 (s, 3H), 1.56 (d, J=6.3 Hz, 3H).
Reaction SMILES: [OH:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[CH2:13][CH2:14][CH3:15].C([O:18][C:19](=[O:49])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH2:36][C:37]([O:39]CC)=[O:38])=[O:29])[CH:25]=[CH:24][C:23]=1[O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]Br)C>CCCCCC.C(OCC)(=O)C>[C:37]([CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:28]([C:26]1[CH:25]=[CH:24][C:23]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:1][C:2]2[CH:12]=[CH:11][C:5]3[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=3[C:3]=2[CH2:13][CH2:14][CH3:15])=[C:22]([CH2:21][CH2:20][C:19]([OH:49])=[O:18])[CH:27]=1)=[O:29])([OH:39])=[O:38]
Reactant: CCOC(=O)CCc1cc(C(=O)c2ccccc2CC(=O)OCC)ccc1OCCCCCBr
Reactant: CCCc1c(O)ccc2c1OCCC2=O
Solvent: CCCCCC
Solvent: CCOC(C)=O
Product: CCCc1c(OCCCCCOc2ccc(C(=O)c3ccccc3CC(=O)O)cc2CCC(=O)O)ccc2c1OCCC2=O
Yield: 23.1 %

Procedure:
Starting with 0.153 g (0.74 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, and 0.394 g (0.74 mmol) of 2-[(5-bromopentyl)oxy]-5-[[2-(2-ethoxy-2-oxoethyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester, the title compound (0.103 g, 26.7% overall yield) was obtained as a white solid, mp 105°-108.5° C. (recrystallized from hexane-ethyl acetate), using the procedure of example 22.
Reaction SMILES: FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][C:11]([N:14]([C:22]2[CH:38]=[CH:37][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:24][CH:23]=2)C(OC(C)(C)C)=O)=[CH:10][CH:9]=1>ClCCl>[N:8]1[CH:13]=[CH:12][C:11]([NH:14][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:37][CH:38]=2)=[CH:10][CH:9]=1
Reactant: CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: CCOC(=O)CCCCCOc1ccc(Nc2ccncc2)cc1

Procedure:
Trifluoroacetic acid (3 ml) was added to a stirred solution of ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]-phenoxy]hexanoate (260 mg) dissolved in dichloromethane (3 ml). After 18 hours the solvents were removed in vacuo and the residual gum dissolved in dichloromethane. This solution was treated with a saturated solution of sodium hydrogen carbonate. The organic phase was washed with water, dried and evaporated. Trituration of the residue with hexane gave the title compound, 120 mg, as a white solid: m.p. 104°-106° C.; NMR (CDCl3) δ 8.22 (2H, d), 7.12 (2H, d), 6.90 (2H, d), 6.64 (2H, dd), 5.82 (1H, s), 4.13 (2H, q), 3.97 (2H, t), 2.34 (2H, t), 1.80 (2H, m), 1.70 (2H, m), 1.53 (2H, m), 1.27 (3H, t); m/e 329 (M+H)+ ; calculated for C19 H24N2O3. 0.25H2O:C, 68.6; H, 7.4; N, 8.4. found: C, 68.8; H, 7.3; N, 8.2%.