Potassium Hydroxide → HCID 71558160, compound

Participants

Reaction Steps

A solution of 4-(2-(3-(tert-butylamino)imidazo[1,2-a]pyridin-6-yl)-4-chlorophenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.35 g, 0.47 mmol) in dichloromethane (3 mL) and trifluoroacetic acid (3 mL) was heated at 80° C. for 16 h in a sealed tube. The mixture was allowed to cool to ambient temperature and was concentrated in vacuo. Methanol (30 mL) was added to the residue. The mixture was filtered and the filtrate concentrated in vacuo. The residue obtained was dissolved in methanol (8 mL) and water (8 mL), and potassium hydroxide (0.079 g, 1.4 mmol) was added. The mixture was heated at 60° C. for 4 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was partitioned between dichloromethane (100 mL) and water (10 mL). The aqueous phase was adjusted to pH 7 with 1 N hydrochloric acid and extracted with dichloromethane (2×30 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative reverse-phase HPLC to afford 4-(2-(3-aminoimidazo[1,2-a]pyridin-6-yl)-4-chlorophenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as an off-white solid in 15% yield (0.037 g): 1H NMR (300 MHz, DMSO-d6) δ 8.70 (s, 1H), 8.13-7.95 (m, 2H), 7.87-7.72 (m, 3H), 7.67-7.52 (m, 3H), 7.29-7.15 (m, 3H), 5.85 (br s, 1H); MS (ES+) m/z 534.8 (M+1), 536.8 (M+1).

Provenance & Evidence