Water → 2-Bromo-6-[4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 69503Notes

Reaction equation

HRID 69503 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:28])[C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]3[S:20][C:21]([Br:27])=[CH:22][C:23]=3[CH2:24][CH2:25]Cl)=[O:18])=[CH:12][CH:11]=2)[CH2:6]1.O.C(OCC)(=O)C>C1COCC1>[Br:27][C:21]1[S:20][C:19]2[C:17](=[O:18])[N:16]([C:13]3[CH:14]=[CH:15][C:10]([N:7]4[CH2:8][CH2:9][C@@H:5]([N:4]([CH3:28])[CH3:3])[CH2:6]4)=[CH:11][CH:12]=3)[CH2:25][CH2:24][C:23]=2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 866351065-Bromo-3-(2-chloro-ethyl)-thiophene-2-carboxylic acid [4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-amide

Product 1

HCID 689912052-Bromo-6-[4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60% in oil; 175.4 mg) was added in small portions to a solution of 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carboxylic acid [4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-amide (612.2 mg) in THF (3.1 mL) at 0° C. The mixture was warmed to room temperature and stirred over night. Water and ethyl acetate was added to the mixture. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 420.37 (C19H22BrN3OS); MS (ESI): 420, 422 (M+H+).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate three times
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customthe solvent was removed in vacuum
  4. customIn this way the product was obtained with molecular weight 420.37 (C19H22BrN3OS)

Sources & evidence

ORD record
ord-50728025cb1a459aadf29e0453dcba3f
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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