Water → Methyl {2-[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-{[(2-hydroxyethyl)amino]carbonyl}-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

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Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.0207 g, 0.052 mmol) and diisopropyl ethylamine (0.075 mL, 0.43 mmol) in DMF (2 mL) under nitrogen was treated with methyl chloroformate (0.0038 mL, 0.049 mmol) at ambient temperature. Water was added (2 mL) and the reaction was concentrated in vacuo. The resulting residue was purified by reversed phase HPLC to provide the title compound from pure fraction concentrated in vacuo as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 3.2 (m, 2 H), 3.4 (m, 5 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.3 (t, J=6.3 Hz, 2 H), 4.9 (t, J=4.9 Hz, 1 H), 7.1 (t, J=8.9 Hz, 2 H), 7.3 (t, J=6.0 Hz, 1 H), 7.4 (m, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.4 (m, 1 H); ES+ MS: 459 (M+H+).

Provenance & Evidence