反应详情

N1-[1-(6-Methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-yl]-ethane-1,2-diamine (213 mg, 0.74 mmol) (from Example 2c) was dissolved in DCM (2 mL) with triethylamine (0.31 mL, 2.2 mmol) and cooled in an ice bath. The cooled solution was treated with 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-sulfonyl chloride and stirred 45 minutes. The reaction mixture was diluted with chloroform and poured into saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with chloroform, and the combined organic layers were washed with brine, dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 0-10% MeOH in CDCl3 (1% NH4OH) to afford the title compound as a white solid (174 mg, 46%): LC/MS m/z 515 (M+H)+; 1H NMR (CDCl3, 400 MHz) δ 8.28 (d, J=5 Hz, 1H), 8.04 (d, J=9 Hz, 1H), 7.43-7.36 (m, 2H), 6.97 (d, J=9 Hz, 1H), 6.30 (d, J=5 Hz, 1H), 4.03 (m, 1H), 3.94 (s, 3H), 3.85 (m, 1H), 3.71 (m, 1H), 3.43 (s, 2H), 3.38 (m, 1H), 3.06 (m, 2H), 2.82 (m, 2H), 2.10 (m, 1H), 1.85 (m, 1H), 1.70-1.60 (m, 1H).

1. temperaturecooled in an ice bath
2. extractionThe aqueous layer was extracted with chloroform
3. washthe combined organic layers were washed with brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. custompurified by column chromatography (silica, 0-10% MeOH in CDCl3 (1% NH4OH)