Triethylamine → HCID 10367877, compound

Participants

Reaction Steps

To the dihydrochloride salt of 3-(3-Amino-propyl)-5-(6-methoxy-[1,5]naphthyridin-4-yl)-oxazolidin-2-one (previous patent) (0.47 g, 1.25 mmol) in CH2Cl2 (14 mL) and MeOH (3.5 mL) was added triethylamine (1.0 mL, 7.2 mmol) and the mixture was stirred at room temperature until all the solid went into solution. 3-Oxo-3,4-dihydro-2H-pyrido[3,2,b][1,4]thiazine-6-carbaldehyde (SB-735214, 0.24 g, 1.24 mmol) was added and the reaction mixture was stirred for 15 hours. Sodium borohydride (0.0519, 1.35 mmol) was added followed by methanol (10 mL). After 30 minutes, the reaction mixture was diluted with chloroform and washed with saturated aqueous NaHCO3 solution, dried (MgSO4), filtered and concentrated. Flash chromatography on silica gel using a gradient of 0-10% MeOH/CHCl3 afforded the product as a white solid (0.32 g, 53%) 1H NMR (400 MHz, CDCl3): δ8.80 (d, J=4.6 Hz, 1H); 8.36 (d, J=9.1 Hz, 1H); 7.70 (d, J=4.5 Hz, 1H); 7.56 (d, J=7.8 Hz, 1H); 7.17 (d, J=9.1 Hz, 1H); 6.92 (d, J=7.8 Hz, 1H); 6.31 (dd, J=8.6, 6.9 Hz, 1H); 4.35 (t, J=9.3 Hz, 1H); 4.04 (s, 3H); 3.75 (s, 2H); 3.48 (s, 2H); 3.47 (dd, J=8.9, 6.9 Hz, 1H); 3.41 (m, 2H); 2.63 (m, 2H), 1.75 (m, 2H). MS (ES) m/e 481 (M+H)+.

Provenance & Evidence