Dimethylformamide → HCID 69482241, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(2-hydroxyethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.025 g, 0.057 mmol) and diisopropyl ethylamine (0.05 mL, 0.29 mmol) in DMF (3 mL) under nitrogen was treated with N,N-dimethyl carbonyl chloride (0.0055 mL, 0.06 mmol) (40° C. After 2½ h the reaction was cooled, concentrated in vacuo, and the resulting residue treated with 1N NaHSO4, filtered, washed with water, and dried in vacuo to provide the title compound as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.73 (s, 1 H), 2.70 (s, 6 H), 3.24-3.30 (m, 3 H), 3.46-3.62 (m, 7 H), 4.12 (s, 2 H), 4.25 (t, J=6.32 Hz, 2 H), 4.62 (t, J=5.19 Hz, 1 H), 6.56 (t, J=5.76 Hz, 1 H), 7.10-7.18 (m, 2 H), 7.37-7.44 (m, 2 H), 8.30 (s, 1 H), 8.53 (d, J=1.69 Hz, 1 H), 10.41 (t, J=5.26 Hz, 1 H); ES+ MS: 516 (M+H+).

Provenance & Evidence