Sodium Hydroxide → Sodium 7-[(4-fluorophenyl)methyl]-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-4-olate

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A solution of 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 (693 mg, 1.436 mmol) in ethanol (20 mL) was treated with 1.009 M NaOH (1.423 mL, 1.436 mmol). The solution was evaporated in vacuo, triturated with Et2O, filtered and dried under high vacuum to provide the product as a white solid: 1H NMR (d6-DMSO) δ 10.65 (1H, s), 8.20 (1H, s), 7.73 (1H, s), 7.35 (2H, dd, J=5, 9 Hz), 7.11 (2H, t, J=9 Hz), 4.16 (2H, t, J=9 Hz), 4.02 (2H, s), 3.24-3.39 (8H, m), 3.25 (3H, s), 2.05 (2H, t, J˜9 Hz), 1.69-1.79 (2H, m); ES− MS: 483 (M−H+).

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