Chloroform → HCID 68539394, compound

Participants

Reaction Steps

N1-[1-(6-Methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-yl]-ethane-1,2-diamine (250 mg, 0.77 mmol) (from Example 2c) was dissolved in MeOH:DCM (8 mL, 1:1) and treated with 3-oxo-3,4-dihydro-2H -pyrido[3,2-b ][1,4]oxazine-6-carbaldehyde (138 mg, 0.77 mmol). After stirring overnight, the reaction mixture was treated with sodium borohydride (29 mg, 0.77 mmol) and stirred 1 h. The reaction mixture was diluted with chloroform and poured into saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted several times with chloroform. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, concentrated to dryness and purified by colume chromatography (silica, 0-10% MeOH in CDCl3 (1% NH4OH)) to afford the title compound as a white solid (140 mg, 40%): LC/MS m/z 450 (M+H)+; 1H NMR (CDCl3, 400 MHz) δ 8.34 (d, J=5 Hz, 1H), 8.07 (d, J=9 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 7.01 (d, J=9 Hz, 1H), 6.88 (d, J=8 Hz, 1H), 6.40 (d, J=5 Hz, 1H), 4.62 (s, 2H), 4.15 (m, 1H), 4.05 (m, 1H), 3.99 (s, 3H), 3.95 (m, 1H), 3.77 (s, 3H), 3.47 (m, 1H), 2.82 (m, 2H), 2.80 (s, 2H), 2.20 (m, 1H), 1.92 (m, 1H).

Provenance & Evidence