反应详情

The 60:40 mixture from the previous step, with the major component being 2-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde, 76 mg, was dissolved in 3 mL THF, and 3 mL absolute ethanol was added. Sodium borohydride (5 mg, 1 eq), was added, and the reaction stirred for 20 minutes, during which time the reaction changed from purple color to colorless. The reaction as quenched with water, and then 1 drop glacial acetic acid was added. The mixture was extracted with ethyl acetate 3×, the organic layers combined and washed with aqueous saturated sodium bicarbonate solution and brine, dried over MgSO4, filtered, and the organic solvent removed under vacuum. The residue was chromatographed over silica gel, eluting first with methylene chloride, and then 3% methanol in methylene chloride, to give the title compound as a white solid, 33 mg, (M+H)+=637.

1. customThe reaction
2. customas quenched with water
3. addition1 drop glacial acetic acid was added
4. extractionThe mixture was extracted with ethyl acetate 3×
5. washwashed with aqueous saturated sodium bicarbonate solution and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customthe organic solvent removed under vacuum
9. customThe residue was chromatographed over silica gel
10. washeluting first with methylene chloride