反应详情

To a nitrogen purged, cooled (0° C.) suspension of 2-(piperidin-1-yl)ethanol (0.577 g, 4.46 mmol) in THF was added sodium hydride (0.196 g of 60% oil dispersion, 4.91 mmol), and the resulting mixture was stirred for 30 minutes. A solution of cis-methyl 4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylate (1.40 g, 4.46 mmol) in THF (14 mL) was added, and the reaction was stirred overnight at RT. The reaction mixture was quenched with water (10 mL) and the product extracted with DCM (30 mL). The organic layer was collected, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-30% of 90/10/1 DCM/MeOH/NH4OH in DCM) to afford cis-methyl 4-(5-nitro-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarboxylate (0.6 g, 33.1% yield). MS m/z=407.2 [M+H]. Calc'd for C20H30N4O5: 406.2.

1. customTo a nitrogen purged
2. temperaturecooled
3. stirringthe reaction was stirred overnight at RT
4. customThe reaction mixture was quenched with water (10 mL)
5. extractionthe product extracted with DCM (30 mL)
6. customThe organic layer was collected
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel chromatography (10-30% of 90/10/1 DCM/MeOH/NH4OH in DCM)