Hydrochloric Acid → 4-aminomethyl-1-furan-3-yl-1H-pyridin-2-one

Participants

Reaction Steps

tert-Butyl (1-furan-3-yl-2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-carbamate (0.18 g, 0.62 mmol) is treated with 4N hydrogen chloride in dioxane in order to remove the Boc protecting group. The hydrochloride salt of 4-aminomethyl-1-furan-3-yl-1H-pyridin-2-one, obtained after concentration of the reaction mixture, is dissolved in N,N-dimethylformamide (4 mL) and is coupled to (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.20 g, 0.62 mmol) in the presence of triethylamine (400 μL). After three hours, the reaction mixture is concentrated under reduced pressure, and the residue is triturated with acetonitrile to provide (4Z)-4-[({[1-(3-furyl)-2-oxo-1,2-dihydropyridin-4-yl]methyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione as a brown powder (0.12 g, 40%).

Provenance & Evidence