4-Toluenesulfonyl chloride → HCID 58970381, compound

Participants

Reaction Steps

2-(Ethoxymethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline (5.1 g, 14 mmol) was treated with mCPBA (5.57 g, 24.2 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (5.14 g, 26.9 mmol) according to a modification of the method described in Part D of Example 8. The reaction was not washed with 10% aqueous sodium hydroxide prior to the addition of ammonium hydroxide. The crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol) and then triturated with ethyl acetate and isolated by filtration to provide 0.843 g of 2-(ethoxymethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-4-amine as off-white needles, mp 187-189° C.

Provenance & Evidence