Trifluoroacetic acid → 2-amino-4-bromo-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide

Participants

Reaction Steps

TFA (2 ml, 26.0 mmol) was added to a solution of bis(1,1-dimethylethyl)(4-bromo-5-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-imidazol-2-yl)imidodicarbonate (1.130 g, 1.616 mmol) in dichloromethane (10 mL). The mixture was stirred at RT overnight. The reaction mixture was stirred with saturated aqueous sodium bicarbonate for 1 hr and the resulting solid was isolated by filtration. A portion (0.100 g) was recrystallized from ethanol to give the title compound (0.071 g, 9%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.16 (br. s., 1H), 7.79-7.85 (m, 1H), 7.72-7.79 (m, 1H), 7.44-7.55 (m, 2H), 7.29-7.39 (m, 1H), 5.53 (br. s., 2H), 4.24-4.68 (m, 2H). ES MS: m/z 498, 500.

Provenance & Evidence