Ethanol → HCID 69480931, compound

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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 (0.019 g, 0.047 mmol) and diisopropyl ethylamine (0.15 mL, 0.86 mmol) in DMF (1.2 mL) under nitrogen was treated with N,N-dimethyl carbonyl chloride (0.0038 mL, 0.041 mmol) at ambient temperature. After 2 h, added EtOH (0.25 mL) and concentrated in vacuo. The resulting residue suspended in 1 N NaHSO4 the refrigerated overnight. 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 2.7 (s, 6 H), 3.3 (s, 4 H), 3.4 (t, J=5.5 Hz, 2 H), 3.6 (t, J=5.3 Hz, 2 H), 4.1 (s, 2 H), 4.2 (t, J=6.0 Hz, 2 H), 4.9 (m, 1 H), 6.5 (m, 1 H), 7.1 (t, J=8.9 Hz, 2 H), 7.4 (m, 2 H), 8.3 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES− MS: 472 (M+H+).

Provenance & Evidence