4-Toluenesulfonyl chloride → HCID 57447032, compound

Participants

Reaction Steps

6-[2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-N-propylhexanamide (4.1 g, 11 mmol) was treated with mCPBA (5.74 g, 33.3 mmol) followed by ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (2.85 g, 14.9 mmol) according to the method described in Part D of Example 8. The crude product was purified by column chromatography on silica gel (eluting with 97:3 dichloromethane:methanol) followed by recrystallization from methanol:water to provide 0.548 g of 6-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-N-propylhexanamide as beige needles, mp 161-162° C.

Provenance & Evidence