反应详情

温度

100 °C

A mixture of tert-butyl 1,4-diazepane-1-carboxylate (81 mg), (1-ethylpiperidin-3-yl)methyl 4-methylbenzenesulfonate (100 mg) and potassium carbonate (186 mg) in acetonitrile (3 mL) was heated to 100° C. in the microwave for 1 hour 15 minutes. The mixture was filtered and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 5% 7M NH3/MeOH in dichloromethane. To a solution of the isolated material (100 mg) in methanol (5 mL) was added 4M hydrochloric acid in dioxane (2 mL). The mixture was stirred for 6 hours at room temperature and then evaporated to give a colourless oil. To a mixture of this oil (150 mg) in dichloromethane (10 mL) and dimethylformamide (1 mL) was added di-iso-propylethylamine (0.31 mL) and 3,4-dichlorophenylisocyanate (100 mg). The mixture was stirred for 15 minutes and then evaporated. The residue was purified using reverse phase HPLC eluting with a mixture of 5-95% acetonitrile in water to give the title compound as a white solid (78 mg, 56%).

1. filtrationThe mixture was filtered
2. customevaporated
3. customThe residue was purified by silica column chromatography
4. washeluting with a gradient of 0 to 5% 7M NH3/MeOH in dichloromethane
5. additionTo a solution of the isolated material (100 mg) in methanol (5 mL) was added 4M hydrochloric acid in dioxane (2 mL)
6. customevaporated
7. customto give a colourless oil
8. stirringThe mixture was stirred for 15 minutes
9. customevaporated
10. customThe residue was purified
11. washeluting with a mixture of 5-95% acetonitrile in water