Dimethylformamide → HCID 69482240, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furanylmethyl)-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 an orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.98-1.34 (m, 1 H), 1.48-1.67 (m, 1 H), 1.67-2.12 (m, 3 H), 2.70 (s, 6 H), 3.32-3.41 (m, 1 H), 3.57 (d, J=18.81 Hz, 1 H), 3.63-3.71 (m, 1 H), 3.78-3.85 (m, 1 H), 4.00 (d, J=1.97 Hz, 2 H), 4.12 (s, 3 H), 4.26 (t, J=6.04 Hz, 2 H), 6.52-6.57 (m, 1 H), 7.14 (t, J=8.70 Hz, 2 H), 7.35-7.43 (m, 2 H), 8.28 (s, 1 H), 8.53 (s, 1 H), 10.46 (s, 1 H); ES+ MS: 512 (M+H+).

Provenance & Evidence