Diisopropylethylamine → HCID 178432875, compound

Participants

Reaction Steps

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (27.9 mg, 0.081 mmol), 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (13.0 mg, 0.081 mmol) and HATU (30.8 mg, 0.081 mmol) in DMF (1.5 ml) was added diisopropylethyl amine (0.028 ml, 0.162 mmol) and the mixture was stirred for 1 hour at rt. The mixture was purified via reverse phase HPLC and neutralized to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-2-methyl-1H-imidazole-5-carboxamide (25 mg, 0.051 mmol, 63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05-8.14 (m, 2H), 7.77 (s, 1H), 7.71 (s, 1H), 7.47 (d, 1H), 7.33 (t, 1H), 4.49 (d, 2H), 2.21 (s, 3H). LC-MS (ES+) m/z 486.94, [M+H].

Provenance & Evidence