Formaldehyde → HCID 67390606, compound

Participants

Reaction Steps

N-(5-chloropyridin-2-yl)-3-hydroxy-2-({4-[2-oxo-1-(2-piperazin-1-ylethyl)-1,2-dihydropyridin-3-yl]benzoyl}amino)benzamide (393 mg) was dissolved in tetrahydrofuran (10 mL), and an aqueous 37% formalin solution (134 μL) and sodium triacetoxyborohydride (436 mg) were added, followed by stirring at room temperature for 9 hours. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 5%). The resulting compound was dissolved in ethyl acetate, and 4 N hydrochloric acid/ethyl acetate was added, followed by stirring at room temperature for 30 minutes. The precipitate formed was collected by filtration and dried under reduced pressure to obtain N-(5-chloropyridin-2-yl)-3-hydroxy-2-[(4-{1-[2-(4-methylpiperazin-1-yl)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoyl)amino]benzamide dihydrochloride (426 mg) as a yellow white solid.

Provenance & Evidence