Toluene → N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine

Participants

Reaction Steps

A Parr vessel was charged with 5% platinum on carbon (0.12 g), purged with nitrogen, and then charged sequentially with toluene (2 mL), N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitro[1,5]naphthyridin-4-amine (6.00 g, 16.4 mmol), toluene (73 mL), and isopropanol (5 mL). The vessel was purged with hydrogen three times and then placed under hydrogen pressure (50 psi, 3.4×105 Pa) for 16 hours. An analysis by high-performance liquid chromatography (HPLC) indicated the presence of starting material. The catalyst was removed by filtration and washed with hot dichloromethane and methanol. The filtrate was concentrated under reduced pressure, and the residue was dissolved in hot methanol (100 mL) and added to a Parr vessel. Catalytic 5% platinum on carbon (0.12 g) was added, and the reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for four hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to provide N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine.

Provenance & Evidence