Triethylamine → HCID 22716712, compound

Participants

Reaction Steps

To a 20 ml dioxane solution containing 783 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoic acid were added 0.48 ml of DPPA, 0.31 ml of triethylamine and 0.89 ml of t-butanol, followed by heating under reflux for 18 hours. After cooling to room temperature and concentration of the reaction mixture under a reduced pressure, ethyl acetate was added to the resulting residue, followed by washing with saturate sodium bicarbonate aqueous solution and saturated brine. The organic layer was concentrated under a reduced pressure and the resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate). To 680 mg portion of 680 mg of thus obtained compound in 5 ml of ethyl acetate was added 5 ml of a 4M hydrogen chloride-ethyl acetate solution under ice cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated and the resulting crude crystals were recrystallized from ethanol-ethyl acetate to obtain 486 mg of 3-(3-aminophenyl)-4-(3-chlorophenyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one monohydrochloride as pale brown crystals.

Provenance & Evidence