Potassium Carbonate → HCID 90389190, compound

Participants

Reaction Steps

To a solution of 5-(5-chloro-2-hydroxyphenyl)-7-(4-methoxybenzyl)imidazo[1,5-a]pyrazin-8(7H)-one (0.12 g, 0.31 mmol) and N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.15 g, 0.33 mmol) in dimethylsulfoxide (2 mL) was added potassium carbonate (0.051 g, 0.37 mmol). The reaction mixture was stirred at ambient temperature for 20 h and diluted with ethyl acetate (80 mL). The organic phase was washed with water (20 mL) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-80% gradient of ethyl acetate in hexanes to afford 4-(4-chloro-2-(7-(4-methoxybenzyl)-8-oxo-7,8-dihydroimidazo[1,5-a]pyrazin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a colorless foam in 83% yield (0.203 g): 1H NMR (300 MHz, CDCl3) δ8.18 (s, 1H), 8.01 (s, 1H), 7.68 (s, 1H), 7.54-7.44 (m, 3H), 7.25-7.13 (m, 3H), 6.89-6.80 (m, 3H), 6.51 (dd, J=9.6, 6.1 Hz, 1H), 6.37 (s, 1H), 6.31 (dd, J=8.4, 2.1 Hz, 1H), 6.17 (d, J=2.1 Hz, 1H), 5.29 (s, 2H), 4.97 (s, 2H), 3.77 (s, 3H), 3.69 (s, 3H), 3.66 (s, 3H); MS (ES+) m/z 806.8 (M+1), 808.8 (M+1).

Provenance & Evidence