Ethanol → HCID 69480274, compound

Participants

Reaction Steps

A solution of ethyl 5-[(4-fluorophenyl)methyl]-3-{[2-(methyl {[(phenylmethyl)oxy]carbonyl}amino)ethyl]amino}-2-pyridinecarboxylate (1.62 g, 3.5 mmol) and ethyl malonyl chloride (1.24 mL, 8.7 mmol) in DCE (50 mL) was heated under nitrogen at reflux for 2 hrs. An additional 0.5 mL of the ethyl malonyl chloride was added and the reaction was stirred at reflux an additional ½ hour. The mixture was cooled, treated with EtOH (25 mL), and then concentrated in vacuo. The residue was purified on silica gel eluting with a gradient between 0 and 100% EtOAc in CH2Cl2 to provide after combination and concentration in vacuo of pure fractions the product as an yellow viscous oil: 1H NMR (400 MHz, DMSO-d6@90° C.) δ ppm 1.11 (t, J=6.77 Hz, 2 H), 1.28 (t, J=7.14 Hz, 3 H), 2.82 (s, 3 H), 3.03 (s, 3 H), 3.34-3.43 (m, 2 H), 3.96 (d, J=5.85 Hz, 2 H), 4.02-4.07 (m, 4 H), 4.27-4.35 (m, 2 H), 5.02 (s, 2H), 7.08 (t, J=8.87 Hz, 2 H), 7.23-7.34 (m, 7 H), 7.70 (s, 1 H), 8.59 (s, 1 H); ES+ MS: 580 (M+H+).

Provenance & Evidence