Hydrochloric Acid → 5-(2-(2,5-dihydro-1H-pyrrol-3-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide hydrochloride

Participants

Reaction Steps

The title compound was prepared in a manner analogous to Example 1, except that tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate was used in place of (2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid and the resulting product, (tert-butyl 3-(2-(2-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate), was converted to the final product by treatment with 50 equivalents of HCl in dioxane. The reaction mixture was concentrated under a vacuum to provide 5-(2-(2,5-dihydro-1H-pyrrol-3-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide hydrochloride. [M+H]+=508.8 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.36 (br. s., 2H), 8.38 (s, 1H), 7.73-7.83 (m, 2H), 7.43 (d, J=7.8 Hz, 1H), 7.23-7.33 (m, 2H), 6.97-7.16 (m, 2H), 5.77 (br. s., 1H), 4.20-4.38 (m, 2H), 3.92 (br. s., 2H), 3.74 (br. s., 2H), 3.64 (t, J=6.7 Hz, 1H), 3.41 (t, J=6.3 Hz, 1H), 3.26-3.36 (m, 1H), 3.12-3.24 (m, 1H)

Provenance & Evidence