Sodium Hydroxide → [7-[(4-fluorophenyl)methyl]-4-hydroxy-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetic acid

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Reaction Steps

A 4N NaOH solution (22 mL) was added dropwise to a 100° C. suspension of 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 (5 g, 11 mmol; the title compound in Example 89) in DMSO (50 mL). The mixture was stirred for 1 h at 100° C., cooled to 10° C., diluted with H2O (10 mL), acidified by dropwise addition of conc. HCl (7 mL), diluted with EtOH and filtered to give the product as a white solid: 1H NMR (d6-DMSO) δ 13.22 (1H, br s), 10.18 (1H, m), 8.55 (1H, s), 8.03 (1H, s), 7.35 (2H, m), 7.11 (2H, m), 4.98 (2H, s), 4.11 (2H, s), 3.52 (4H, m), 3.28 (3H, s).

Provenance & Evidence