Diisopropylethylamine → HCID 178437659, compound

Participants

Reaction Steps

To a mixture of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (197 mg, 0.573 mmol), 4-chloro-2-ethyl-1H-imidazole-5-carboxylic acid (100 mg, 0.573 mmol) and HATU (218 mg, 0.573 mmol) in DMF (4.0 ml) was added diisopropylethyl amine (0.200 ml, 1.146 mmol) and the mixture was stirred for 1 hr at rt. The reaction mixture was diluted with ethyl acetate and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-2-ethyl-1H-imidazole-5-carboxamide (135 mg, 0.269 mmol, 47% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.11 (s, 2H), 7.80 (s, 1H), 7.74 (s, 1H), 7.50 (dd, 1H), 7.36 (t, 1H), 4.52 (d, 2H), 2.58 (q, 2H), 1.16 (t, 3H). LC-MS (ES+) m/z 501.10, [M+H].

Provenance & Evidence