Reaktion #582182

Reaktionsgleichung

tetrahydrofuran

1-(1-(2-(2-hydroxy-6-methoxy-3-((methylamino)carbonyl)phenyl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide

1,1′-carbonyldiimidazole

→

subject compound

1-{1-[2-(7-Methoxy-3-methyl-2,4-dioxo-3,4-dihydro-2H-1,3-benzoxazin-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxamide

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe obtained mixture was then heated
2. 2
   Temperaturto reflux under nitrogen atmosphere for 5 minutes
3. 3
   Temperaturthe obtained mixture was then heated
4. 4
   Temperaturto reflux under nitrogen atmosphere for 45 minutes
5. 5
   Sonstigethe solvent was then removed under a reduced pressure
6. 6
   workup.ADDITIONThereafter, 294 mg of 1,1′-carbonyldiimidazole was added to the residue
7. 7
   TemperaturThe reaction mixture was heated
8. 8
   Temperaturto reflux under nitrogen atmosphere for 30 minutes
9. 9
   TemperaturThe reaction solution was cooled to a room temperature
10. 10
    Sonstigethe solvent was then removed under a reduced pressure
11. 11
    workup.ADDITIONWater was added to the residue
12. 12
    Filtrationthe precipitate was collected by filtration
13. 13
    WaschenThe precipitate was washed with diethyl ether
14. 14
    Sonstigethe solvent was removed under a reduced pressure
15. 15
    workup.ADDITIONEthyl acetate was added to the residue
16. 16
    Filtrationfollowed by filtration

Vorschrift

30 ml of anhydrous tetrahydrofuran was added to 408 mg of 1-(1-(2-(2-hydroxy-6-methoxy-3-((methylamino)carbonyl)phenyl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide. Thereafter, 294 mg of 1,1′-carbonyldiimidazole was added thereto. The obtained mixture was then heated to reflux under nitrogen atmosphere for 5 minutes. Thereafter, 5 ml of N,N-dimethylformamide was added to the reaction solution, and the obtained mixture was then heated to reflux under nitrogen atmosphere for 45 minutes. The reaction solution was cooled to a room temperature, and the solvent was then removed under a reduced pressure. Thereafter, 294 mg of 1,1′-carbonyldiimidazole was added to the residue. The reaction mixture was heated to reflux under nitrogen atmosphere for 30 minutes. The reaction solution was cooled to a room temperature, and the solvent was then removed under a reduced pressure. Water was added to the residue, and the precipitate was collected by filtration. The precipitate was washed with diethyl ether. It was then suspended in ethanol, and the solvent was removed under a reduced pressure. Ethyl acetate was added to the residue, followed by filtration, so as to obtain 451 mg of the subject compound.

Quelle