2-Methoxyethylamine → 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (21 mg, 0.048 mmol) was dissolved in ethanol (1 mL) and [2-(methyloxy)ethyl]amine (0.05 mL) was added. This solution was heated in a microwave at 140° C. for 20 minutes. The resulting suspension was concentrated under reduced pressure and 1 N hydrochloric acid was added to bring the mixture to a pH of 3. The resulting white solid was collected by vacuum filtration to yield 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (19.8 mg, 86%). 1H NMR (CDCl3) δ 10.07 (m, 1 H), 8.52 (s, 1 H), 7.30-7.28 (m, 2 H), 7.22-7.18 (m, 2 H), 7.02-6.92 (m, 4 H), 6.70 (s, 1 H), 3.95 (s, 2 H), 3.65-3.60 (m, 2 H), 3.55-3.52 (m, 2 H), 3.33 (s, 3 H); MS m/z 459 (M+23).

Provenance & Evidence