反应详情

温度

180 °C

Benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (55 mg), ethyl {[(4-amino-1-adamantyl) carbonyl]amino}acetate (54 mg) and triethylamine (80 μl) were dissolved in N-methyl-2-pyrrolidone (0.55 ml) and stirred at 180° C. for 1 hour using a microwave reaction system. To the reaction solution were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate), the obtained compound was dissolved in dioxane (1.1 ml) and methanol (1.1 ml), 10% palladium on carbon (50% wet) was added, and catalytic reduction was performed for 4 hours at ambient temperature at 1 atm. Methanol, dioxane, and 1M hydrochloric acid were added, and the precipitated solid was dissolved and filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to obtain 4-({5-[(2-ethoxy-2-oxoethyl)carbamoyl]adamantan-2-yl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (18 mg).

1. customa microwave reaction system
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over magnesium sulfate
5. customevaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate)
7. dissolutionthe obtained compound was dissolved in dioxane (1.1 ml)
8. additionmethanol (1.1 ml), 10% palladium on carbon (50% wet) was added
9. waitcatalytic reduction was performed for 4 hours at ambient temperature at 1 atm
10. additionMethanol, dioxane, and 1M hydrochloric acid were added
11. dissolutionthe precipitated solid was dissolved
12. filtrationfiltered
13. customto remove the catalyst
14. concentrationThe filtrate was concentrated under reduced pressure