4-Toluenesulfonyl chloride → HCID 57447072, compound

Participants

Reaction Steps

mCPBA (1.18 g, 6.86 mmol) was added to a solution of 1-(4-morpholin-4-yl-4-oxobutyl)-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine (1.80 g, 4.90 mmol) in chloroform (25 mL); the reaction was stirred for two hours at ambient temperature. Ammonium hydroxide (10 mL) was added followed by p-toluenesulfonyl chloride (1.03 g, 5.39 mmol). The reaction was stirred for one hour and partitioned between saturated aqueous sodium bicarbonate (75 mL) and dichloromethane (70 mL). The aqueous layer was extracted with dichloromethane (2×25 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting brown solid was triturated twice with acetonitrile and then purified by column chromatography using a HORIZON HPFC system (an automated, modular high-performance flash purification product available from Biotage, Inc.; Charlottesville, Va., USA) using a FLASH 40+M cartridge (also available from Biotage, Inc.). The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform:CMA in a gradient from 100:0 to 75:25. The resulting solid was dried under high vacuum at 80° C. to provide 0.583 g of 1-(4-morpholin-4-yl-4-oxobutyl)-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as an off-white powder, mp 196-197° C.

Provenance & Evidence