反应详情

A solution of 4-chloro-N-(6-hydroxy-pyridin-3-yl)-benzamide (0.50 g, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 g, 2.00 mmol) and triethylamine (0.20 g, 2.00 mmol) in dimethylformamide (10 mL) was stirred overnight at room temperature. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane, filtered over a short pad of silicagel and washed with ethyl acetate:heptane 50:50. The solvent was evaporated in vacuo and the residue was redissolved in acetonitrile and hydrofluoric acid (min. 40% in water, 0.50 mL) was added. After stirring overnight at room temperature the solvent was evaporated in vacuo. Dichloromethane and triethylamine (1 mL) were added and the solution was extracted twice with water, dried over sodium sulphate, filtered and evaporated in vacuo. Crystallisation from ethyl acetate:heptane yielded the title compound (321 mg, 43% yield).

1. customThe solvent was evaporated in vacuo
2. dissolutionThe residue was dissolved in dichloromethane
3. filtrationfiltered over a short pad of silicagel
4. washwashed with ethyl acetate:heptane 50:50
5. customThe solvent was evaporated in vacuo
6. dissolutionthe residue was redissolved in acetonitrile
7. additionhydrofluoric acid (min. 40% in water, 0.50 mL) was added
8. customwas evaporated in vacuo
9. additionDichloromethane and triethylamine (1 mL) were added
10. extractionthe solution was extracted twice with water
11. dry with materialdried over sodium sulphate
12. filtrationfiltered
13. customevaporated in vacuo
14. customCrystallisation from ethyl acetate