4-Toluenesulfonyl chloride → HCID 67052344, compound

Participants

Reaction Steps

mCPBA (0.985 g, 5.71 mmol) was added to a suspension of N-{3-[2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-2-methylpropanamide (1.41 g, 4.08 mmol) in chloroform (20 mL). The reaction mixture was allowed to stir for 4 hours at room temperature. Concentrated ammonium hydroxide (5 mL) followed by p-toluenesulfonyl chloride (0.854 g, 4.48 mmol) were added and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with chloroform (25 mL) and brine (40 mL) and transferred to a separatory funnel. The aqueous layer was extracted with chloroform (20 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a tan solid. Trituration with methanol and isolation by filtration afforded 0.670 g of N-{3-[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-2-methylpropanamide.

Provenance & Evidence