Diisopropylethylamine → (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-N-(1,5-naphthyridin-4-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a vessel charged with (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoyl chloride (50 mg, 0.152 mmol) were added DCM (606 μL), 1,5-naphthyridin-4-amine (commercially available from Astatech Inc., Bristol, Pa.) (24 mg, 0.167 mmol), and DIEA (55.6 μL, 0.318 mmol) respectively. The vessel was sealed and shaken overnight at 40° C. The mixture was dried under reduced pressure and purified using a 25 g, 15 m spherical silica column (Interchim) ramping 0-100% EtOAc in heptane from 0-100% to elute product, which was lyophilized from MeOH/H2O to yield (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-N-(1,5-naphthyridin-4-yl)benzamide (64 mg, 96%) as an off-white powder. 1H NMR (400 MHz, DMSO-d6) δ=10.63 (s, 1H), 9.01 (dd, J=1.6, 4.2 Hz, 1H), 8.93 (d, J=5.0 Hz, 1H), 8.54 (d, J=5.1 Hz, 1H), 8.46 (dd, J=1.6, 8.5 Hz, 1H), 8.01-7.96 (m, 2H), 7.89 (dd, J=4.3, 8.6 Hz, 1H), 7.76-7.70 (m, 2H), 7.43-7.37 (m, 2H), 7.36-7.22 (m, 3H), 5.57 (s, 1H), 1.67 (s, 3H), 0.94 (s, 3H). m/z (ESI) 439.2 (M+H)+.

Provenance & Evidence