Water → HCID 57682767, compound

HRID 494936Notes

Reaction equation

HRID 494936 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][O:9][C:5]=2[C:4]=1[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH2:32])=[O:31])[CH:28]=3)[CH:23]=[CH:22]2)[CH2:17][CH2:16]1.[H-].[Na+].[CH3:35]I.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][O:9][C:5]=2[C:4]=1[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:35])=[O:31])[CH:28]=3)[CH:23]=[CH:22]2)[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11582846HCID 11582846, compound

Product 1

HCID 57682767HCID 57682767, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

65 mg of 1-(1-(2-(6-methoxy-3-methylbenz[d]isoxazol-7-yl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide obtained in Example 1 was dissolved in 1 ml of N,N-dimethylformamide, and then, 7.2 mg of 60% sodium hydride was added thereto. The reaction solution was stirred at room temperature for 5 minutes, and 11.2 μl of methyl iodide was then added to the reaction solution. After completion of the reaction, water and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium bicarbonate aqueous solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate), so as to obtain 17 mg of the subject compound.

Workup

  1. additionwere added to the reaction solution
  2. customso as to separate an organic layer
  3. washThe obtained organic layer was washed with a saturated sodium bicarbonate aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the drying agent
  6. filtrationby filtration
  7. concentrationthe organic layer was concentrated under a reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-00f97caae6ee48579d32c90023f22dce
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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