Trifluoroacetic acid → HCID 59026713, compound

Participants

Reaction Steps

1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (Example 11, 0.300 g, 0.833 mmol) was combined with platinum (IV) oxide (0.03 g) and trifluoroacetic acid (5 mL), and the mixture was placed under hydrogen pressure (45 psi, 3.1×105 Pa) for 24 hours. An analysis by liquid chromatography/mass spectrometry indicated the presence of starting material. The catalyst was removed by filtration, and the trifluoroacetic acid was removed under reduced pressure. The residue was combined with trifluoroacetic acid (5 mL) and platinum (IV) oxide (0.10 g), and the reaction was again placed under hydrogen pressure (45 psi, 3.1×105 Pa) for 24 hours. The catalyst was removed by filtration, and the trifluoroacetic acid was removed under reduced pressure. The resulting oil was dissolved in 6 N hydrogen chloride in ethanol and stirred for 30 minutes. The solvent was removed under reduced pressure, and the residue was dissolved in water. The solution was adjusted to pH 14 with the addition of a few drops of 50% w/w sodium hydroxide, and the resulting mixture was stirred for 30 minutes. A precipitate was present and was isolated by filtration, purified by column chromatography on silica gel (5% to 10% CMA in chloroform), triturated with diethyl ether, filtered, and dried to provide 0.0382 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a white powder, mp 227.0-228.0° C.

Provenance & Evidence