Hydrochloric Acid → 1-[2-(Dimethylamino)-2-oxoethyl]-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

A mixture of ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate(49.2 g, 115 mmol) and 2-methoxyethylamine (14.8 mL, 172 mmol) in NMP (400 mL) was heated at 95-115° C. for 1-2 h. The mixture was cooled to rt, diluted with water (600 mL) and acidified with 1N HCl (72 mL). The precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.23 (1H, br t, J=5 Hz), 8.51 (1H, s), 7.75 (1H, s), 7.32 (2H, dd, J=9, 6 Hz), 7.12 (2H, t, J=9 Hz), 5.12 (2H, s), 4.11 (2H, s), 3.54-3.44 (4H, m), 3.27 (3H, s), 3.12 (3H, s), 2.82 (3H, s); HRMS calcd for C23H25FN4O5+H+: 457.1887.Found: 457.1884.

Provenance & Evidence