Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]12[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH:11]C(=O)O[C:7]2=[O:8]>O1CCCC1>[NH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=1[C:7]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]
Reactant: O=c1[nH]c2ccccc2c(=O)o1
Reactant: C1CCNC1
Solvent: C1CCOC1
Product: Nc1ccccc1C(=O)N1CCCC1
Temperature: 25 °C
Reaction time: 1.5 h
Yield: 69.6 %

Procedure:
Pyrrolidine (2.46 g, 34.6 mmol) was added dropwise to isatoic anhydride (3.76 g, 23.05 mmol) in tetrahydrofuran (25 mL) at room temperature. The solution was stirred at room temperature for 1.5 hours under a nitrogen atmosphere. The volatiles were removed by evaporation under reduced pressure. The residue was slurried in toluene (50 mL) and the volatiles were removed by evaporation under reduced pressure (2×). The residue was dissolved in hot toluene, then allowed to cool to room temperature. The solution was placed in a freezer for 16 hours to produce a precipitate. The precipitate was filtered and dried to give 3.05 g of crude 1-(2-aminobenzoyl)-pyrrolidine. The crude material (2.65 g) was purified by column chromatography over silica gel using 5-20% ethyl acetate in hexanes. The best fractions were combined and the volatiles were removed by evaporation under reduced pressure. The residue was taken up in dichloromethane (50 mL) and washed with 0.5N sodium hydroxide solution (2×25 mL), washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to yield 1.35 g of 1-(2-aminobenzoyl)pyrrolidine.
Reaction SMILES: [C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][CH2:20][C:21]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)=[CH:27][CH:26]=1)([OH:24])[CH2:22][OH:23]>CC#N>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:32]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([C:21]([OH:24])([CH2:20][OH:19])[CH2:22][OH:23])=[CH:30][CH:29]=2)=[O:33])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]
Reactant: CC(C)(C)c1cc(CN)n(-c2cccc(Cl)c2)n1
Reactant: O=C(Nc1ccc(C(O)(CO)CO)cc1)Oc1ccccc1
Solvent: CC#N
Product: CC(C)(C)c1cc(CNC(=O)Nc2ccc(C(O)(CO)CO)cc2)n(-c2cccc(Cl)c2)n1
Reaction time: 16 h
Yield: 66.7 %

Procedure:
To a stirred MeCN (9 mL) solution of (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine (102 mg, 0.387 mmol, 1.0 eq), TEA (0.214 mL, 1.55 mmol, 4.0 eq) followed by phenyl 4-(1,2,3-trihydroxypropan-2-yl)phenylcarbamate (119 mg, 0.395 mmol, 1.02 eq) was added at RT and the mixture was stirred for 16 h at reflux, then it was concentrated under vacuum and the residue purified by CC using EtOAc as eluent to get 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(1,2,3-trihydroxypropan-2-yl)phenyl)urea (122 mg; 67%).