Acetonitrile → HCID 86687618, compound

Participants

Reaction Steps

A round-bottom flask was charged with perfluorophenyl 1-(5-chloro-2-methoxyphenyl)isoquinoline-6-sulfonate (INTERMEDIATE XXXX, 150.33 mg, 0.291 mmol), 1,2,4-thiadiazol-5-amine (35.4 mg, 0.350 mmol), and cesium carbonate (285 mg, 0.874 mmol). acetonitrile (1457 μl) was added, and the mixture was stirred for 1.5 h. The mixture was diluted with EtOAc and 0.5 N aq. HCl. The layers were separated, and the organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was concentrated from MeOH. The residue was taken up in MeOH, sonicated, and filtered on a membrane filter. The collected solid was washed with MeOH (3×), dried under a stream of N2 (g), then dried under vacuum to give 1-(5-chloro-2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (100.0 mg, 0.231 mmol, 79% yield) as a cream-colored solid. 1H NMR (400 MHz, DMSO-d6) δ=8.69 (d, J=5.7 Hz, 1H), 8.58 (d, J=1.7 Hz, 1H), 8.49 (s, 1H), 8.15 (d, J=5.5 Hz, 1H), 7.89 (dd, J=1.9, 8.9 Hz, 1H), 7.75 (d, J=8.9 Hz, 1H), 7.59 (dd, J=2.7, 8.9 Hz, 1H), 7.40 (d, J=2.7 Hz, 1H), 7.26 (d, J=9.0 Hz, 1H), 3.65 (s, 3H). m/z (ESI) 432.9 (M+H)+.

Provenance & Evidence