2-Methoxyethylamine → 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

A mixture of ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate (1.13 g, 2.50 mmol) and 2-methoxyethylamine (1.1 mL, 12.5 mmol) in isopropanol (20 mL) was heated at reflux for 3 hrs. After cooling, the resulting slurry was diluted with isopropanol (10 mL) and filtered. The precipitate was partitioned between CH2Cl2 and 1N NaHSO4. After separating the layers, the aqueous phase was back-extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered and evaporated in vacuo to provide the product as a white solid. The isopropanol was evaporated in vacuo and the residue was partitioned between CH2Cl2 and 1N NaHSO4. After separating the layers, the aqueous phase was back-extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered and evaporated in vacuo to provide an additional crop of the product as a white solid: 1H NMR (CDCl3) δ 10.27 (1H, br m), 8.55 (1H, s), 8.06 (1H, s), 7.24 (2H, m), 6.99 (2H, t, J=8.6 Hz), 4.35 (2H, t, J=7 Hz), 4.14 (2H, s), 3.65 (2H, m), 3.59 (2H, m), 3.50 (2H, t, J=7 Hz), 3.44 (2H, m), 3.42 (3H, s), 2.31 (2H, t, J=8 Hz), 1.97 (2H, m); ES+ MS: 483 (M+H+).

Provenance & Evidence