Trifluoroacetic acid → HCID 178426122, compound

Participants

Reaction Steps

To a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-methylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (73.0 mg, 0.131 mmol) in DCM (5 ml) was added TFA (1.5 mL) and the reaction mixture was stirred for 4 hours at room temperature. The reaction was quenched with saturated sodium bicarbonate and the organic layer was separated. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-chloro-5-methylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (32 mg, 0.075 mmol, 57% yield). 1H NMR (400 MHz, DMSO-d5) δ ppm 12.74-13.45 (m, 1H), 7.97-8.44 (m, 1H), 7.73 (s, 1H), 7.44 (d, 1H), 7.29 (t, 1H), 6.98 (s, 1H), 6.69 (d, 2H), 4.27-4.76 (m, 2 H), 2.23 (s, 3H). LC-MS (ES+) m/z 427.91, [M+H].

Provenance & Evidence