Dimethylcarbamoyl Chloride → HCID 69482781, compound

Participants

Reaction Steps

A solution of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(methyl {[(phenylmethyl)oxy]carbonyl}amino)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.255 g, 0.48 mmol) in CH2Cl2 (20 mL) was combined with diisopropylethylamine (0.42 mL, 2.4 mmol), dimethylcarbamic chloride (0.22 mL, 2.4 mmol) and Pd/C (0.030 g, 10% w/w). The resulting suspension was flushed with nitrogen and evacuated several times the charged with hydrogen under a balloon and stirred at ambient temperature overnight. The reaction mixture was filtered, washed with CH2Cl2, and concentrated in vacuo. The residue was washed with EtOAc:Hexanes 1:1, filtered and the filtrate was concentrated in vacuo. The residue was triturated with water and the resulting suspension was filtered to afford the title compound as an off-white crystalline solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.25 (t, J=7.05 Hz, 3 H), 2.59 (s, 6 H), 2.80 (s, 3 H), 3.26-3.30 (m, 2 H), 4.17 (s, 2 H), 4.23 (q, J=7.16 Hz, 2 H), 4.32 (t, J=6.21 Hz, 2 H), 7.11-7.18 (m, 2 H), 7.38-7.43 (m, 2 H), 8.11 (s, 1 H), 8.50 (d, J=1.47 Hz, 1 H); ES+ MS: 471 (M+H+).

Provenance & Evidence