Sodium Hydroxide → HCID 76591490, compound

HRID 494934Notes

Reaction equation

HRID 494934 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:32]([NH2:34])=[O:33])[CH:30]=4)[CH:25]=[CH:24]3)[CH2:19][CH2:18]2)=[CH:5][C:6]2[C:12](=O)[CH2:11][CH2:10][CH2:9][O:8][C:7]=2[CH:14]=1.Cl.[O:36]([NH2:38])[CH3:37].C([O-])(=O)C.[Na+].[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O1CCCC1.CO>[CH3:1][O:2][C:3]1[C:4]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:32]([NH2:34])=[O:33])[CH:30]=4)[CH:25]=[CH:24]3)[CH2:19][CH2:18]2)=[CH:5][C:6]2[C:12](=[N:38][O:36][CH3:37])[CH2:11][CH2:10][CH2:9][O:8][C:7]=2[CH:14]=1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate2×HCID 521874O-Methylhydroxylamine hydrochloride2×HCID 57682902HCID 57682902, compound

Product 1

HCID 76591490HCID 76591490, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

97 mg of 1-(1-(2-(8-methoxy-5-oxo-2,3,4,5-tetrahydrobenzo[b]oxepin-7-yl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide was dissolved in a mixed solution consisting of 4 ml of methanol, 2 ml of tetrahydrofuran, and 2 ml of chloroform. Thereafter, 105 mg of methoxylamine hydrochloride and 103 mg of sodium acetate were added to the reaction solution, and the obtained mixture was then stirred at room temperature. At the midpoint of the reaction, 1 g of methoxylamine hydrochloride and 1 g of sodium acetate were further added thereto. After completion of the reaction, a 1 N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution, and chloroform 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 a saturated sodium chloride 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 solidified from t-butyl methyl ether-ethyl acetate, so as to obtain 70 mg of the subject compound.

Workup

  1. additionwere further added
  2. customAfter completion of the reaction
  3. customso as to separate an organic layer
  4. washThe obtained organic layer was washed with a saturated sodium bicarbonate aqueous solution
  5. dry with materiala saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
  6. customAfter removing the drying agent
  7. filtrationby filtration
  8. concentrationthe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-2ba4a6f25dd040d390eb6c264e966267
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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