4-Toluenesulfonyl chloride → HCID 66619871, compound

Participants

Reaction Steps

A solution of tert-butyl 9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridine-8-carboxylate (1 g, 3 mmol) in dichloromethane (100 mL) was treated with MCPBA (1 g, 77% purity), and the reaction was stirred for two hours. Analysis by LC/MS indicated the presence of starting material, and additional MCPBA (1 g) was added. The next day, the reaction cooled in an ice bath and was treated with 100 mL of concentrated ammonium hydroxide. The reaction was stirred for several minutes, and then p-toluenesulfonyl chloride (730 mg, 3.8 mmol) was added. The reaction was stirred for several minutes, removed from the ice bath, and stirred for three hours at room temperature. Water was added, and the mixture was extracted with dichloromethane. The combined organic fractions were purified by automated flash chromatography on silica gel (eluting with a gradient of 2% ammonium hydroxide methanol as the polar component in dichloromethane). The resulting oil was triturated in diethyl ether to provide a yellow solid, which was isolated by filtration to provide 0.64 g of tert-butyl 6-amino-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridine-8-carboxylate.

Provenance & Evidence