Trifluoroacetic acid → 1-(2-Bromo-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-YL)isoquinoline-6-sulfonamide

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Reaction Steps

To a solution of 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (INTERMEDIATE DD, 100 mg, 0.157 mmol) in DCM (1574 μl) was added TFA (60.6 μl, 0.787 mmol). The mixture was stirred at room temperature. After 2 h, LC/MS showed mainly the desired product. The reaction mixture was concentrated and dissolved in 3 ml of DMSO. This solution was injected onto the reverse phase HPLC (Xbridge 10 μm, C18, 19×100 mm column eluting with 0.1% NH4OH in ACN and water as the mobile phase) ultimately affording 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (10.6 mg, 0.021 mmol). MS (ESI): 514.8 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ ppm 7.68 (d, J=8.87 Hz, 1H), 7.76 (d, J=7.80 Hz, 1H), 7.90-7.98 (m, 2H), 8.22-8.26 (m, 2H), 8.48 (s, 1H), 8.65 (m, 1H), 8.76 (d, J=5.66 Hz, 1H).

Provenance & Evidence