Trifluoroacetic acid → HCID 178527556, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.149 g, 0.22 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (1 mL) at 0° C. The reaction mixture was stirred for 2 h at 0° C. The mixture was concentrated in vacuo and the residue was suspended in methanol (20 mL) and filtered. The filtrate was concentrated in vacuo and the residue triturated in diethyl ether (5 mL) and suspended in water (2 mL). Lyophilization affored 4-(2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzene-sulfonamide as the corresponding beige trifluoroacetate salt in 75% yield (0.11 g): 1H NMR (300 MHz, DMSO-d6) δ9.11 (s, 1H), 8.37 (s, 1H), 7.84 (s, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.64 (dd, J=10.2, 6.5 Hz, 1H), 7.62 (d, J=2.6 Hz, 1H), 7.54 (d, J=8.3 Hz, 1H), 7.49 (dd, J=8.7, 2.5 Hz, 1H), 7.27 (d, J=8.7 Hz, 1H), 7.11 (dd, J=10.4, 6.5 Hz, 1H), (NH not observed); 19F NMR (282 MHz, DMSO-d6) δ−76.6 (s, 3F), −113.0 (d, J=15.8 Hz, 1F), −139.0 (d, J=15.9 Hz, 1F); MS (ES+) m/z 519.7 (M+1), 521.7 (M+1).

Provenance & Evidence