Pyridine → HCID 10362522, compound

Participants

Reaction Steps

Difluoroacetic acid (0.031 mL, 0.48 mmol) is added to a solution of 1-[4-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,3-dihydro-1H-pyridin-4-one hydrochloride (0.150 g, 0.44 mmol) in DMF (1.5 mL) with pyridine (0.071 mL, 0.88 mmol), followed by addition of diisopropylcarbodiimide (0.076 mL, 0.48 mmol). The mixture is stirred at r.t. for 1 h. Most of the solvent is removed under high vacuum, and the product is purified by silica gel column chromatography (eluent: 2% MeOH in DCM). The chromatography is repeated (eluent: 1% MeOH in DCM) to afford N-{3-[3-Fluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl} difluoroacetamide as a white solid. Yield 0.065 g (39%). MS (m/z): 384 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 9.36 (t, J=5.5 Hz, 1H), 7.82–7.49 (m, 4H), 6.44 (t, J=53.6 Hz, 1H), 5.18 (d, J=7.7 Hz, 1H), 5.03–4.98 (m, 1H), 4.38–4.32 (m, 1H), 4.07 (t, J=7.4 Hz, 2H), 3.97 (dd, J=6.3 and 9.3 Hz, 1H), 3.72 (t, J=5.5 Hz, 1H), 3.51–3.49 (m, 2H), 2.69–2.64 (m, 2H).

Provenance & Evidence