Potassium Carbonate → HCID 90389133, compound

Participants

Reaction Steps

To a stirred mixture of N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.89 g, 2.0 mmol) and potassium carbonate (0.83 g, 6.0 mmol) in dimethylsulfoxide (15 mL) at ambient temperature was added 4-chloro-2-(imidazo[1,2-a]pyrimidin-5-yl)phenol (0.45 g, 2.0 mmol). The mixture was stirred at ambient temperature for 16 h and diluted with ethyl acetate (50 mL) and water (20 mL). 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 80-100% gradient of ethyl acetate in hexanes to afford 4-(4-chloro-2-(imidazo[1,2-a]pyrimidin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.47 g). This solid was dissolved in dichloromethane (15 mL) and trifluoroacetic acid (2 mL) was added. The mixture was stirred for 2 h at ambient temperature and concentrated in vacuo. The residue was triturated in a mixture of ethyl ether and ethyl acetate to afford 4-(4-chloro-2-(imidazo[1,2-a]pyrimidin-5-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a colorless solid in 53% yield (0.55 g): 1H NMR (300 MHz, DMSO-d6) δ8.94 (d, J=4.2 Hz, 1H), 8.52 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.07 (d, J=1.2 Hz, 1H), 7.91-7.69 (m, 3H), 7.61 (d, J=4.2 Hz, 1H), 7.56-7.47 (m, 1H), 7.43 (d, J=8.7 Hz, 1H); MS (ES+) m/z 520.7 (M+1), 522.7 (M+1).

Provenance & Evidence