Trifluoroacetic acid → HCID 86687669, compound

Participants

Reaction Conditions

Reaction Steps

2-(6-(N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-4-fluoroisoquinolin-1-yl)benzamide was dissolved in pyridine (0.6 mL) and cooled to 0° C. POCl3 (0.023 mL, 0.243 mmol) was added. The reaction was stirred for 5 minutes at room temperature. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was dissolved in DCM and TFA (0.1 mL, 1.298 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The reaction was concentrated and purified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM) to afford 1-(2-cyanophenyl)-4-fluoro-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=13.02 (br. s., 1H), 8.84 (d, J=1.6 Hz, 1H), 8.57 (d, J=1.3 Hz, 1H), 8.13-8.03 (m, 2H), 7.99-7.86 (m, 2H), 7.83-7.73 (m, 2H), 7.68-7.51 (m, 2H), 7.31 (d, J=4.5 Hz, 1H), 6.90 (d, J=4.6 Hz, 1H). m/z (ESI) 410.9 (M+H)+.

Provenance & Evidence