Thionyl Chloride → HCID 89813997, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.287 mL, 3.93 mmol) was added to a solution of (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoic acid (0.128 g, 0.393 mmol) in DCM (2.5 mL) and the mixture was heated at 40° C. for 1 hour. The reaction mixture was concentrated to afford (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoyl chloride as a yellow-orange solid. The yellow-orange solid was dissolved in DCM (2.5 mL) and the solution was cooled to 0° C. 1,5-Naphthyridin-4-amine (commercially available from Astatech Inc., Bristol, Pa.) (0.063 g, 0.433 mmol) and N,N-diisopropylethylamine (0.144 mL, 0.826 mmol) were added and the ice bath was removed. The resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then concentrated and the residue was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methyl-N-(1,5-naphthyridin-4-yl)benzamide (0.070 g, 0.155 mmol, 39% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.65 (s, 3H), 2.44 (s, 3H), 5.54 (s, 1H), 7.17-7.51 (m, 6H), 7.61 (d, J=2.15 Hz, 1H), 7.67 (d, J=8.51 Hz, 1H), 7.86 (dd, J=8.56, 4.16 Hz, 1H), 8.44 (dd, J=8.56, 1.61 Hz, 1H), 8.54 (d, J=5.09 Hz, 1H), 8.81-9.09 (m, 2H), 10.31 (s, 1H). m/z (ESI) 453 (M+H)+.

Provenance & Evidence