4-Toluenesulfonyl chloride → HCID 58970363, compound

Participants

Reaction Steps

A modification of the methods described in Part F of Example 53 was used to treat 6-[2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide (1.70 g, 5.0 mmol) with mCPBA (3.34 g of 70-77% purity) followed by ammonium hydroxide (5.5 mL), and p-toluenesulfonyl chloride (0.95 g). After the amination reaction was stirred for one hour, a precipitate was present and was isolated by filtration and washed with chloroform and water. The precipitate was triturated with 2-propanol (7.5 mL/g at 97° C.), and the mixture was filtered hot. The isolated solid was dried overnight under vacuum and then in a vacuum oven for six days at 65° C. The product was then sonicated in 1 M aqueous sodium hydroxide for 15 minutes, isolated by filtration, washed with deionized water, and dried in a vacuum oven for three days at 90° C. to provide 0.32 g of 6-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]hexanamide as a yellow solid, mp 215-217° C.

Provenance & Evidence