Hydrochloric Acid → HCID 71259325, compound

Participants

Reaction Steps

A 10-mL round-bottom flask was charged with N-(2,4-dimethoxybenzyl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (35.79 mg, 0.056 mmol) and methanol (1 mL). Hydrogen chloride (4M in 1,4-dioxane) (141 μl, 0.563 mmol) was added, and the resulting solution was stirred for 45 min. The reaction mixture was loaded onto a 500 mg SCX-2 ion exchange column (Silicycle, Quebec City, Canada). The column was eluted with methanol, then with a solution of 2N ammonia in methanol. The basic fractions were combined and concentrated. The residue was purified further by chromatography on silica gel (0 to 10% MeOH/DCM) to give 3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (12.05 mg, 0.025 mmol, 44.1% yield) as a cream colored solid. 1H NMR (400 MHz, DMSO-d6) δ=8.35 (br. s., 1 H), 7.90 (d, J=1.1 Hz, 1 H), 7.62 (d, J=1.3 Hz, 2 H), 7.56-7.31 (m, 4 H), 7.12 (s, 1 H), 6.27 (d, J=1.9 Hz, 1 H), 3.79 (s, 3 H), 3.23 (s, 3 H). m/z (ESI) 485.1 (M+H)+.

Provenance & Evidence