Tetrahydrofuran → HCID 57682807, compound

HRID 495000Notes

Reaction equation

HRID 495000 reaction equation
[O:1]1CCCC1.[OH:6][C:7]1C(C(NC)=O)=[CH:11][CH:10]=[C:9]([O:17][CH3:18])[C:8]=1[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([C:36]([NH2:38])=[O:37])[CH:34]=3)[CH:29]=[CH:28]2)[CH2:23][CH2:22]1.[C:39]([N:46]1[CH:50]=[CH:49]N=[CH:47]1)(N1C=CN=C1)=[O:40]>CN(C)C=O>[CH3:18][O:17][C:9]1[CH:10]=[CH:11][C:49]2[C:50](=[O:1])[N:46]([CH3:47])[C:39](=[O:40])[O:6][C:7]=2[C:8]=1[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([C:36]([NH2:38])=[O:37])[CH:34]=3)[CH:29]=[CH:28]2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 57682769HCID 57682769, compound

Product 1

HCID 57682807HCID 57682807, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. temperatureThe obtained mixture was then heated
  2. temperatureto reflux under nitrogen atmosphere for 5 minutes
  3. temperaturethe obtained mixture was then heated
  4. temperatureto reflux under nitrogen atmosphere for 45 minutes
  5. customthe solvent was then removed under a reduced pressure
  6. additionThereafter, 294 mg of 1,1′-carbonyldiimidazole was added to the residue
  7. temperatureThe reaction mixture was heated
  8. temperatureto reflux under nitrogen atmosphere for 30 minutes
  9. temperatureThe reaction solution was cooled to a room temperature
  10. customthe solvent was then removed under a reduced pressure
  11. additionWater was added to the residue
  12. filtrationthe precipitate was collected by filtration
  13. washThe precipitate was washed with diethyl ether
  14. customthe solvent was removed under a reduced pressure
  15. additionEthyl acetate was added to the residue
  16. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-776b488aff8340559df54af1cc0341e6
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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