Dimethylformamide → HCID 178432445, compound

Participants

Reaction Steps

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (33.6 mg, 0.098 mmol), 4-bromo-2-methyl-1H-imidazole-5-carboxylic acid (20 mg, 0.098 mmol) and HATU (37.1 mg, 0.098 mmol) in DMF (5 ml) was added diisopropylethyl amine (0.034 ml, 0.195 mmol) and the mixture was stirred for 20 minutes at rt. The 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]-2-methyl-1H-imidazole-5-carboxamide trifluoroacetate (15.0 mg, 0.023 mmol, 24% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.23 (t, 1H), 8.11 (s, 1H), 7.79 (s, 1H), 7.74 (s, 1H), 7.50 (d, 1H), 7.36 (t, 1H), 4.49 (d, 2H), 2.26 (s, 3H). LC-MS (ES+) m/z 531.10, [M+H].

Provenance & Evidence