Methanol → HCID 86687496, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 3-chloro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (Example 249) (35.79 mg, 0.072 mmol), sodium methoxide (25.1 mg, 0.465 mmol), and MeOH (477 μl). The vial was sealed and heated in a 100° C. heating bath for 1 h. The mixture was diluted with DMSO (0.5 mL) to solubilize the solids, and an additional portion of sodium methoxide (25.1 mg, 0.465 mmol) was added. The vial was sealed and heated to 120° C. for 1.5 h. The mixture was cooled to room temperature and diluted with EtOAc, then washed with 1N aq. HCl, washed with water, washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (0 to 5% MeOH/DCM) to give 3-methoxy-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (23.2 mg, 0.047 mmol, 65.4% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm=12.88 (s, 1H), 8.40 (s, 1H), 7.61-7.56 (m, 3H), 7.55-7.48 (m, 3H), 7.28 (d, J=4.6 Hz, 1H), 6.87 (d, J=4.6 Hz, 1H), 3.95 (s, 3H), 3.76 (s, 3H). m/z (ESI) 496.2 (M+H)+.

Provenance & Evidence