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

Participants

Reaction Steps

To a solution of N-(4-methoxybenzyl)-1-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (100 mg, 0.158 mmol) in DCM (1578 μl) was added TFA (60.8 μl, 0.789 mmol). The reaction mixture was stirred at room temperature. After 2 hours, LC/MS showed mainly product. Purification was done using a Phenomenex Gemini 5 μm, C18, 110 Å, 150×30 mm column with 0.1% TFA in ACN and water as mobile phase to afford 1-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (6.2 mg, 0.012 mmol, 7.65%). MS (ESI): 514.0 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ ppm 7.19-7.22 (m, 2H), 7.80 (s, 2H), 7.85 (d, J=8.01 Hz, 1H), 8.01-8.06 (m, 2H), 8.11 (d, J=5.77 Hz, 1H), 8.37 (br. s., 2H), 8.47 (s, 1H), 8.54 (s, 1H), 8.61 (d, J=5.66 Hz, 1H).

Provenance & Evidence