Dichloromethane → HCID 86687494, compound

Participants

Reaction Steps

A flask was charged with 3-chloro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (Intermediate RRR) (58.43 mg, 0.094 mmol), DCM (1 mL), and TFA (0.5 mL) to give a yellow solution (8:45 am). After 30 min of stirring at RT, the mixture was diluted with MeOH and concentrated. The residue was purified by chromatography on silica gel (0-10% MeOH/DCM) to give 47 mg of a light yellow solid. The solid was concentrated from DCM (2×), then taken up in DCM and filtered. The collected solid was washed with DCM (2×), then dried under vacuum for 10 min to give 3-chloro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-n-(thiazol-2-yl)isoquinoline-6-sulfonamide as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm=12.95 (s, 1H), 8.57 (d, J=1.8 Hz, 1H), 8.39 (s, 1H), 7.87 (dd, J=1.8, 8.9 Hz, 1H), 7.72 (d, J=8.9 Hz, 1H), 7.61 (d, J=7.7 Hz, 1H), 7.56-7.48 (m, 2H), 7.30 (d, J=4.7 Hz, 1H), 6.90 (d, J=4.6 Hz, 1H), 3.76 (s, 3H). m/z (ESI) 500.2 (M+H)+.

Provenance & Evidence