Diisopropylethylamine → 2-Phenyl-pyrimidine-5-carboxylic acid (2-sulfamoyl-ethyl)-amide

Reaction equation

[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][CH2:17][CH2:18][S:19]([NH2:22])(=[O:21])=[O:20].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[S:19]([CH2:18][CH2:17][NH:16][C:13]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH:11]=1)=[O:14])(=[O:21])(=[O:20])[NH2:22]

Participants

Procedure

To a solution of 2-phenyl-pyrimidine-5-carboxylic acid chloride (1.51 mmol) and 2-amino-ethanesulfonic acid amide (1.51 mmol) in DCM (15 mL) is added diisopropylethylamine (4.53 mmol). The mixture is stirred at room temperature overnight. The mixture is concentrated in vacuo. The residue is washed with water and DCM to afford 2-phenyl-pyrimidine-5-carboxylic acid (2-sulfamoyl-ethyl)-amide as a solid. MS: 307 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 3.25 (q, 2H), 3.67 (m, 2H), 6.93 (s, N—H), 7.47-7.60 (m, 3H), 8.36-8.48 (m, 2H), 8.92-9.15 (m, N—H), 9.16-9.36 (m, 2H); IC50=55 nM.