Trifluoroacetic acid → HCID 178439240, compound

Participants

Reaction Steps

4-chloro-N-[(4-chloro-3-{[3-cyano-5-(2-propen-1-yl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.034 g, 0.059 mmol) dissolved in DCM (2.5 mL) was treated with TFA (2.5 mL) at 25° C. for 3 days with stirring. The reaction mixture was concentrated to dryness and the residue was purified by mass-directed HPLC on a SunFire prep C-18 column eluted with 30 to 85% CH3CN/H2O (0.1% formic acid buffer). Appropriate fractions were combined, concentrated to dryness, chased twice with ethanol and twice with toluene to remove residual water to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(2-propen-1-yl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (0.022 g, 0.049 mmol, 84% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.19 (br. s., 1H), 8.28 (br. s., 1H), 7.78 (s, 1H), 7.50 (d, J=8.52 Hz, 1H), 7.44 (s, 1H), 7.35 (t, J=7.62 Hz, 1H), 7.25 (br. s., 1H), 7.15 (br. s., 1H), 5.85-6.03 (m, 1H), 5.09 (d, J=6.46 Hz, 1H), 5.06 (s, 1H), 4.53 (d, J=4.39 Hz, 2H), 3.41 (d, J=6.46 Hz, 2H). LC-MS (ES−) m/z 443.10, 445.17 [M−1]. LC-MS (ES+) m/z 445.05, 447.08 [M+H].

Provenance & Evidence