Hydrochloric Acid → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamothioyl)-2-(2-fluorophenyl)acetamide di-hydrochloride

Participants

Reaction Steps

A mixture of aniline 219 (100 mg, 0.29 mmol, scheme 47) and 2-(2-fluorophenyl)acetyl isothiocyanate (115 mg, 0.58 mmol) in THF (3 mL) was stirred for 1 hour, loaded directly onto a column containing silica gel and eluted sequentially with EtOAc and EtOAc/MeOH (100:1), to produce a white solid. This material was suspended in MeOH (5 mL) and HCl (1.0M in ether, 1 mL) was added to form a clear solution that was evaporated to dryness. The residue was washed with ether, suspended in H2O, and lyophilized to afford the title compound (80 mg, 45% yield) as a yellowish solid. 1H-NMR (DMSO-d6) δ (ppm): 12.42(s, 1H), 11.88 (s, 1H), 8.65(d. 1H, J=5.5 Hz), 8.20 (s, 1H), 8.05(d, 1H, J=1.7Hz), 7.74 (s, 1H), 7.58-7.55 (m, 3H) 7.39-7.32 (m, 2H), 7.21-7.16 (m, 2H), 6.82(d, 1H, J=5.5 Hz), 4.02 (s, 3H), 3.93(s, 2H), MS (m/z): 536.2 (M+H) (found).

Provenance & Evidence