Hydrochloric Acid → 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

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Reaction Steps

To a stirred solution of 1,3,4-thiadiazol-2-amine (0.083 g, 0.8 mmol) in anhydrous dimethylsulfoxide (1.0 mL) at ambient temperature was added potassium tert-butoxide (0.092 g, 0.8 mmol). The mixture was stirred at ambient temperature for 10 minutes and 4-chlorophenyl 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluorobenzenesulfonate (0.15 g, 0.27 mmol) was added. The reaction mixture was stirred for 1 h at ambient temperature and water (6 mL), 1 M hydrochloric acid (0.85 mL) and ethyl acetate (25 mL) were added. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-10% gradient of methanol in ethyl acetate to afford 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide as a beige solid in 42% yield (0.060 g): 1H NMR (300 MHz, DMSO-d6) δ8.76 (s, 1H), 7.79 (d, J=2.6 Hz, 1H), 7.71-7.57 (m, 5H), 7.37-7.28 (m, 3H), 7.00 (dd, J=7.0, 0.9 Hz, 1H); MS (ES+) m/z 519.8 (M+1), 521.8 (M+1).

Provenance & Evidence