Dimethylformamide → HCID 69482099, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)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 was triturated with EtOAc and water, filtered, and dried in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.84 (s, 1 H), 2.39-2.47 (m, 4 H), 2.52-2.57 (m, 2 H), 2.71 (s, 6 H), 3.23-3.31 (m, 2 H), 3.44-3.55 (m, 2 H), 3.56-3.62 (m, 4 H), 4.12 (s, 2 H), 4.25 (t, J=6.32 Hz, 2 H), 6.57 (t, J=5.55 Hz, 1 H), 7.09-7.18 (m, 2 H), 7.41 (dd, J=8.70, 5.62 Hz, 2 H), 8.30 (s, 1 H), 8.53 (s, 1 H), 10.40 (t, J=5.90 Hz, 1 H); ES+ MS: 541 (M+H+).

Provenance & Evidence