4-Toluenesulfonyl chloride → tert-butyl[2-(4-amino-2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate

Participants

Reaction Steps

Using the general method of Example 5 Part B, a solution of tert-butyl[2-(2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (27.45 g, 76.1 mmol) in chloroform (500 mL) was treated with 3-chloroperoxybenzoic acid (25.6 g of 77% max, 114 mmol) and the resulting 5-oxide was aminated using ammonium hydroxide (150 mL) and para-toluenesulfonyl chloride (17.4 g, 91.3 mmol) to provide 41.83 g of crude tert-butyl[2-(4-amino-2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate as a brown solid. A portion (˜32 g) of the crude material was dissolved in dichloromethane and then washed with 1 N hydrochloric acid (×3). The organic layer was allowed to stand for several days and a precipitate formed. This material was isolated by filtration to provide 7.0 g of tert-butyl[2-(4-amino-2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate as an off white solid.

Provenance & Evidence