Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[C:4]2[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:5]2=[N:6][CH:7]=1.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N:28]=[C:29]=[O:30]>O1CCCC1>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:3]1[C:2]([NH:1][C:29]([NH:28][C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[F:20])=[O:30])=[CH:7][N:6]=[C:5]2[S:8][C:9]([CH2:11][CH3:12])=[CH:10][C:4]=12
Reactant: CCc1cc2c(-c3ccccc3Cl)c(N)cnc2s1
Reactant: O=C=Nc1ccc(F)cc1F
Solvent: C1CCOC1
Product: CCc1cc2c(-c3ccccc3Cl)c(NC(=O)Nc3ccc(F)cc3F)cnc2s1
Temperature: 25 °C
Reaction time: 18 h
Yield: 93.9 %

Procedure:
To a solution of 5-amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine (288 mg) in tetrahydrofuran (3 ml) was added 2,4-difluorophenyl isocyanate (0.13 ml) and the mixture was stirred at room temperature for 18 hours, and then the solvent was distilled off. To the residue was added isopropyl ether to obtain N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea as crystals (416 mg, 93.9 %). Colorless prisms were obtained by recrystallization from acetone-hexane, mp: 217°-218° C.
Reaction SMILES: [CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[NH2:18])[CH2:3]1.N1C=CC=CC=1.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>ClCCl.O>[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:13])([F:15])[F:14])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[NH:18][S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[CH2:3]1
Reactant: CCS(=O)(=O)Cl
Reactant: CC1(C)CC(c2ccccc2N)Nc2ccc(C(F)(F)F)cc21
Solvent: ClCCl
Solvent: O
Solvent: c1ccncc1
Product: CCS(=O)(=O)Nc1ccccc1C1CC(C)(C)c2cc(C(F)(F)F)ccc2N1
Temperature: 25 °C
Reaction time: 3 h

Procedure:
To a solution of 2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline (150 mg) and pyridine (200 μL) in dichloromethane (3 mL) was added ethanesulfonylchloride (44 μL) at ice-bath under nitrogen. After addition, the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, concentrated. The residue was purified by HPLC to give ethanesulfonic acid [2-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide. LC/MS m/e obsd. (ESI+) [(M+H)+] 412.9.
Reaction SMILES: [Br:1][C:2]1[C:11]([C@@H:12]([OH:15])[CH2:13][OH:14])=[C:10]([CH3:16])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([Sn](=O)CCCC)CCC.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].CCN(CC)CC>C(Cl)Cl>[CH3:34][C:33]1[CH:35]=[CH:36][C:30]([S:27]([O:14][CH2:13][C@@H:12]([C:11]2[C:2]([Br:1])=[C:3]3[C:8](=[CH:9][C:10]=2[CH3:16])[N:7]=[CH:6][CH:5]=[CH:4]3)[OH:15])(=[O:29])=[O:28])=[CH:31][CH:32]=1
Reactant: Cc1cc2ncccc2c(Br)c1[C@@H](O)CO
Reactant: Cc1ccc(S(=O)(=O)Cl)cc1
Agent: CCCC[Sn](=O)CCCC
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: Cc1ccc(S(=O)(=O)OC[C@H](O)c2c(C)cc3ncccc3c2Br)cc1
Temperature: 25 °C

Procedure:
To a stirred solution of (R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol (197 mg, 0.70 mmol) in CH2Cl2 (97 mL), dibutyltinoxide (3.3 mg, 0.01 mmol), TsCl (150 mg, 0.79 mmol), and Et3N (0.12 mL, 0.83 mmol) were added at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was quenched with saturated aqueous NH4Cl, and then diluted with CH2Cl2. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 5 to 100% ethyl acetate/hexanes) to give (R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate. LCMS-ESI+ (m/z): [M+H]+ calc'd for C19H19BrNO4S: 436.02; Found: 436.1.
Reaction SMILES: [C:1]([OH:22])(=O)[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].ClC(OCCCC)=O.Cl.C(N(CC)CC)C.Cl.[CH3:40][O:41][C:42](=[O:47])[C@H:43]([CH2:45][OH:46])[NH2:44].Cl>C(#N)C.CO.C(N(CC)CC)C>[CH3:40][O:41][C:42](=[O:47])[C@H:43]([CH2:45][OH:46])[NH:44][C:1](=[O:22])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]
Reactant: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Reactant: COC(=O)[C@@H](N)CO
Agent: CCCCOC(=O)Cl
Agent: Cl
Solvent: CCN(CC)CC
Solvent: CC#N
Solvent: CO
Product: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@@H](CO)C(=O)OC
Temperature: -15 °C
Reaction time: 0.5 h
Yield: 91.7 %

Procedure:
Arachidonic acid (152 g, 0.5 mmol) and triethylamine (52 mg, 0.51 mmol) were dissolved in 3 ml of dry acetonitrile and chilled to −15° C., and 70 mg (0.51 mmol) of butyl chloroformate was added. After 30 min, the mixture free of the precipitated triethylamine hydrochloride was pipetted in a solution of L-serine methyl ester hydrochloride (156 mg, 1 mmol) and 0.14 ml of triethylamine in 1 ml of methanol, stirring was continued for 15 min at −15° C., then that mixture was allowed to warm to room temperature. After 2 h, 0.5 M HCl was added, and the mixture was extracted with ether (20 ml). The extract was washed with water, then dried with Na2SO4, and evaporated in vacuo. The residue was dissolved in 2 ml of chloroform and purified by column (2×2 cm) chromatography on aluminum oxide (basic, Brockmann II). Elution of the column with chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions gave 186 mg (95%) of desired N-arachidonoyl-L-serine methyl ester as oil: TLC (system A) Rf 0.5.