Triethyl orthoacetate → 1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c][1,5]naphthyridine

Participants

Reaction Conditions

Reaction Steps

Triethyl orthoacetate (2.8 mL, 15.2 mmol) was added to a solution of N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine (prepared in Part B of Example 12, 3.4 g, 10.1 mmol) and pyridine hydrochloride (0.023 g, 0.20 mmol) in toluene (100 mL), and the reaction was heated at 110° C. under a nitrogen atmosphere for 15.5 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane. The work-up and purification procedures described in Part D of Example 12 were followed with the modification that the silica column was eluted with 5% methanol in ethyl acetate. 1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c][1,5]naphthyridine (1.15 g) was obtained as a light gray solid.

Provenance & Evidence