4-Toluenesulfonyl chloride → 5-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide

Participants

Reaction Steps

5-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide (4.4 g, 14 mmol) was treated with mCPBA (4.28 g, 24.8 mmol), ammonium hydroxide (40 mL), and p-toluenesulfonyl chloride (5.24 g, 27.4 mmol) according to a modification of the method described in Part F of Example 34. At the completion of the amination reaction, a precipitate was present and was isolated by filtration. The precipitate was triturated and sonicated with acetone, isolated by filtration, and dried in a vacuum oven at 80° C. to provide 1.28 g of 5-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide as a tan powder, mp 202-203° C.

Provenance & Evidence