Diisopropylethylamine → HCID 178510237, compound

Participants

Reaction Steps

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (36.1 mg, 0.105 mmol), 4-bromo-1H-imidazole-5-carboxylic acid (20.0 mg, 0.105 mmol) and diisopropylethyl amine (0.0366 mL, 0.210 mmol) in DMF (5 ml) was added HATU (39.8 mg, 0.105 mmol) and the mixture was stirred at rt for 30 minutes. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-bromo-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (11.0 mg, 0.021 mmol, 20% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.27-8.50 (m, 1H), 8.11 (s, 1H), 7.76-7.89 (m, 2H), 7.74 (s, 1H), 7.50 (dd, 1H), 7.37 (t, 1H), 4.50 (d, 2H). LC-MS (ES+) m/z 516.90, [M+H].

Provenance & Evidence