Potassium Carbonate → HCID 89555368, 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 (0.41 g, 0.93 mmol) (prepared according to PCT Published Patent Application No. WO 2010/079443) and potassium carbonate (0.38 g, 2.8 mmol) in dimethylsulfoxide (4 mL) at ambient temperature was added 2-(6-aminopyridin-2-yl)-4-chlorophenol (0.19 g, 0.93 mmol). The mixture was stirred at ambient temperature for 16 h and diluted with ethyl acetate (50 mL) and water (20 mL). The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-50% gradient of ethyl acetate in hexanes to afford 4-(2-(6-aminopyridin-2-yl)-4-chlorophenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide in 83% yield (0.49 g): 1H NMR (300 MHz, CDCl3) δ 8.16 (s, 1H), 7.84 (d, J=2.7 Hz, 1H), 7.51-7.34 (m, 3H), 7.14 (d, J=8.7 Hz, 1H), 7.01 (d, J=8.7 Hz, 1H), 6.97 (d, J=7.5 Hz, 1H), 6.42-6.26 (m, 3H), 6.17 (d, J=2.4 Hz, 1H), 5.25 (s, 2H), 4.39 (s, 2H), 3.75 (s, 3H), 3.63 (s, 3H); MS (ES+) m/z 645.6 (M+1), 647.6 (M+1).

Provenance & Evidence