反应详情

A mixture of N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(6-fluoro-3′-formyl-3-biphenylyl)methyl]-1,3-benzenedicarboxamide (150 mg, 0.226 mmol), 1,2-dimethylpiperazine (45.7 mg, 0.40 mmol), sodium triacetoxyborohydride (95 mg, 0.45 mmol) and AcOH (18 μl, 0.314 mmol) in 1,2-dichloroethane (DCE) (6 mL) was stirred overnight at room temperature. LC/MS showed that the reaction was complete. The reaction was diluted with EtOAc; the organic layer washed with dilute aq. NaOH, then sat. aq. NaCl and dried [Na2SO4], then concentrated to a viscous taffy. The material was purified on a Gilson HPLC using reverse phase (acetonitrile-water with 0.1% TFA). Fractions containing the desired product were combined, the MeOH removed, the aqueous layer treated with EtOAc and 1N NaOH. The mixture was vigorously extracted with EtOAc (2×), the extract was washed with a small amount of sat. aq. NaCl; dried [Na2SO4], then concentrated to a glassy, creamy tan, coloured foam (0.1002 g). LC-MS m/z 761.5 (M+H)+, 0.76 min (ret time).

1. washthe organic layer washed with dilute aq. NaOH
2. dry with materialsat. aq. NaCl and dried [Na2SO4]
3. concentrationconcentrated to a viscous taffy
4. customThe material was purified on a Gilson HPLC
5. additionFractions containing the desired product
6. customthe MeOH removed
7. additionthe aqueous layer treated with EtOAc and 1N NaOH
8. extractionThe mixture was vigorously extracted with EtOAc (2×)
9. washthe extract was washed with a small amount of sat. aq. NaCl
10. dry with materialdried [Na2SO4]
11. concentrationconcentrated to a glassy, creamy tan, coloured foam (0.1002 g)
12. customLC-MS m/z 761.5 (M+H)+, 0.76 min (ret time)