Sodium Sulfate → 1-[2-((2S)-2-{[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]methyl}-4-morpholinyl)ethyl]-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

Participants

Reaction Steps

To a solution of 1-{2-[(2S)-2-(aminomethyl)-4-morpholinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one (0.100 g, 0.314 mmol) in 1:1 (MeOH/CH2Cl2) (25 mL) were added 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde) (for a synthesis see WO2004/058144 Example 2(c) or WO03/087098, Example 19(d)) (0.052 g, 0.314 mmol) and sodium sulphate (0.100 g) and the resulting solution stirred for 18 hours at ambient temperature. Na(OAc)3BH (0.200 g, 0.942 mmol) was added and the solution stirred an additional 2 h. The reaction mixture was concentrated onto silica gel and chromatographed to yield a colorless oil and further purified by HPLC(CH3CN/H2O) to yield the title compound as a white powder (0.049 g, 33%).

Provenance & Evidence