Ethylamine → (5r)-n-Ethyl-3-[4-(4-oxo-3,4-dihydro-1(2h)-pyridinyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide

Participants

Reaction Steps

To a stirred solution of 3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylic acid ethyl ester (EXAMPLE 69, within Step 6, 108 mg, 0.31 mmol) in MeOH (1 mL) is added EtNH2 (2 mL, 4.0 mmol, 2.0 M solution in THF). The reaction mixture is stirred for 1 h at room temperature. Solvent is removed and the residue purified by column chromatography (10% MeOH/CH2Cl2) to give the title compound as a pale yellow solid (100 mg, 93%), 1H NMR (300 MHz, DMSO) δ 8.46 (t, 1H), 7.65–7.38 (m, 4H), 5.05 (dd, 1H), 4.99 (d, 1H), 4.27 (t, 1H), 4.01 (dd, 1H), 3.87 (t, 2H), 3.20–3.10 (m, 2H), 1.04 (t, 3H); MS for C17H18FN3O4 m/z 348.5 (M+H)+.

Provenance & Evidence