4-Toluenesulfonyl chloride → HCID 57447015, compound

Participants

Reaction Steps

2-(Ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c]quinoline (6.9 g, 18 mmol) was treated with mCPBA (7.9 g, 35 mmol), concentrated ammonium hydroxide (50 mL of 29%), and p-toluenesulfonyl chloride (6.0 g, 32 mmol) according to a modification of the method described in Part E of Example 3. The mCPBA addition was carried out at 0° C., and the reaction was carried out in dichloromethane (150 mL). The crude product was triturated with 2:1 ethyl acetate:hexane (15 mL), and the resulting solid was isolated by filtration, washed with 30:70 ethyl acetate:hexane, recrystallized twice from methanol:water, and dried overnight in a vacuum oven at 70° C. to provide 2-(ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c]quinolin-4-amine as yellow crystals, mp 201-203° C.

Provenance & Evidence