Trifluoroacetic acid → HCID 71711242, compound

Participants

Reaction Steps

1-(2-Chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide (INTERMEDIATE V, 0.068 g, 0.108 mmol) was dissolved in 1 mL of DCM and TFA (0.1 mL, 1.298 mmol) was added. The reaction was stirred for 10 minutes. The material was concentrated, dissolved in acetonitrile and loaded onto an ion exchange column (pre-wetted with acetonitrile). The column was flushed several times with acetonitrile, then the product was liberated by flushing the column several times with about 1M HCl solution in MeOH/EtOAc (made by adding acetyl chloride to a MeOH/EtOAc mixture). The second filtrate was concentrated to afford 1-(2-chloro-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide as a purple solid. 1H NMR (400 MHz, DMSO-d6) δ=8.42 (s, 1 H), 7.99 (s, 1 H), 7.80 (d, J=8.1 Hz, 1 H), 7.63 (d, J=8.0 Hz, 1 H), 7.01 (d, J=2.1 Hz, 1 H), 6.80 (dd, J=1.9, 8.3 Hz, 1 H), 6.08 (d, J=8.4 Hz, 1 H), 3.61 (t, J=4.0 Hz, 2 H), 3.40 (t, J=4.4 Hz, 2 H). m/z (ESI) 475.8 (M+H)+.

Provenance & Evidence