Dimethylformamide → HCID 69480157, 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 (0.06 mL, 0.63 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 purified on silica gel by prep TLC (9:1 CH2Cl2:MeOH). Pure bands were collected to provide the title compound as an off-white solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.98 (s, 3 H), 3.46-3.54 (m, 2 H), 3.68 (d, J=4.76 Hz, 2 H), 3.71 (s, 4 H), 3.77-3.88 (m, 2 H), 4.17 (s, 2 H), 4.36 (t, J=7.23 Hz, 2 H), 5.31 (s, 1 H), 6.14 (s, 1 H), 7.02 (t, J=8.79 Hz, 2 H), 7.22-7.25 (m, 2 H), 8.07 (s, 1 H), 8.58 (s, 1 H), 10.51 (s, 1 H); ES+ MS: 487 (M+H+).

Provenance & Evidence