4-Toluenesulfonyl chloride → HCID 57447044, compound

Participants

Reaction Steps

2-Methyl-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline (4.8 g, 15 mmol) was treated with mCPBA (5.95 g, 25.9 mmol) followed by ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (5.49 g, 28.8 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. After the amination reaction was stirred for two hours, water was added. Following the work-up procedure, the chromatographic purification was carried out eluting with 90:10 dichloromethane:methanol. The resulting product was triturated with ethyl acetate and isolated by filtration to provide 2-methyl-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-4-amine as brown needles, mp 166-169° C.

Provenance & Evidence