m-Chloroperbenzoic acid → HCID 69506838, compound

Participants

Reaction Steps

mCPBA (1.80 g, 7.28 mmol) was added to a solution of 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanamide (1.63 g, 5.20 mmol) in chloroform (50 mL); the reaction was stirred for three hours at ambient temperature. An analysis by LC/MS indicated the reaction was incomplete; therefore, additional mCPBA (1.2 equivalents) was added. The reaction was stirred for two hours and then diluted with saturated aqueous sodium bicarbonate (75 mL) and chloroform (75 mL). The aqueous layer was extracted with dichloromethane (2×30 mL) and chloroform (12×20 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.34 g of 4-[2-(ethoxymethyl)-5-oxido-1H-imidazo[4,5-c][ 1,5]naphthyridin-1-yl]butanamide as an orange solid.

Provenance & Evidence