4-Toluenesulfonyl chloride → HCID 57447104, compound

Participants

Reaction Steps

A modification of the method described in Part F of Example 53 was used to treat 6-(2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide (1.18 g, 3.8 mmol) with mCPBA (2.54 g of 70-77% purity) followed by ammonium hydroxide (4 mL), and p-toluenesulfonyl chloride (0.72 g). After the amination reaction was stirred for 15 minutes, a precipitate was present and was isolated by filtration. The precipitate was purified by chromatography using a HORIZON HFPC system (silica cartridge, eluting with 0-55% CMA in chloroform) and dried for three days at 90° C. to provide 0.34 g of 6-(4-amino-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide as a light yellow solid, mp 220-221° C.

Provenance & Evidence