HCID 61129737, compound → HCID 178464667, compound
Reaction equation
CS[C:3]([N:7]1[CH2:11][C:10]([CH3:13])([CH3:12])[CH:9]=[N:8]1)=[N:4][CH2:5][CH3:6].[Br:14][C:15]1[CH:20]=[C:19]([S:21](=[O:24])(=[O:23])[NH2:22])[CH:18]=[CH:17][C:16]=1[NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28]>C(#N)C>[Br:14][C:15]1[CH:20]=[C:19]([S:21](=[O:24])(=[O:23])[N:22]=[C:3]([N:7]2[CH2:11][C:10]([CH3:12])([CH3:13])[CH:9]=[N:8]2)[NH:4][CH2:5][CH3:6])[CH:18]=[CH:17][C:16]=1[NH:25][C:26](=[O:31])[C:27]([F:29])([F:30])[F:28]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3.41 g (1 mol equiv.) N-Ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 6.24 g (1.05 mol equiv.) N-(2-Bromo-4-sulfamoyl-phenyl)-2,2,2-trifluoro-acetamide were added to 100 mL acetonitrile. The reaction mixture was refluxed overnight, and subsequently volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and extracted with 2N NaOH, and the organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (Et2O) afforded 7.1 g (83%) N-(2-bromo-4-{[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-sulfamoyl}-phenyl)-2,2,2-trifluoro-acetamide. 1H NMR (400 MHz, CDCl3) δ 1.18 (t, J=7.3 Hz, 3H), 1.24 (s, 6H), 3.43-3.51 (m, 2H), 3.79 (br.s., 2H), 6.78 (s, 1H), 7.93 (dd, J=8.6, 2.0 Hz, 1H), 8.19 (d, J=2.0 Hz, 1H), 8.39 (d, J=8.6 Hz, 1H), 8.61 (br.s., 1H).