Dimethylformamide → HCID 69482278, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-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. Extracted the mixture 3× with EtOAc and concentrated the organics. The residue was then dissolved in EtOAc and washed with saturated NaHCO3 (aqueous) then concentrated the organics. Triturated the residue with Et2O, filtered, and dried in vacuo to provide the title compound as an orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.66-1.79 (m, 2 H), 1.76-1.93 (m, 1 H), 2.35 (t, J=6.18 Hz, 6 H), 2.70 (s, 6 H), 3.19-3.31 (m, 2 H), 3.40-3.48 (m, 2 H), 3.53-3.63 (m, 4 H), 4.11 (s, 2 H), 4.25 (s, 2 H), 6.54-6.59 (m, 1 H), 7.14 (t, J=8.84 Hz, 2 H), 7.37-7.44 (m, 2 H), 8.17-8.39 (m, 1 H), 8.52 (s, 1 H), 10.38 (s, 1 H); ES+ MS: 555 (M+H+).

Provenance & Evidence