Potassium Carbonate → 5-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

HRID 13340Notes

Reaction equation

HRID 13340 reaction equation
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[C:30]([O:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=2)=[CH:29][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[N:27][CH:26]=[CH:25][N:24]=3)[NH:22][C:18]=2[CH:17]=1)=O>CO.O>[CH3:41][S:38]([C:35]1[CH:36]=[CH:37][C:32]([O:31][C:30]2[C:16]([CH:12]3[CH2:13][CH2:14][CH2:15][NH:11]3)=[CH:17][C:18]3[NH:22][C:21]([C:23]4[CH:28]=[N:27][CH:26]=[CH:25][N:24]=4)=[N:20][C:19]=3[CH:29]=2)=[CH:33][CH:34]=1)(=[O:40])=[O:39]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 231455992,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Product 1

HCID 231455085-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

55 mg of potassium carbonate was added to a solution of 40 mg of 2,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone in a mixture of 1.6 ml of methanol and 0.4 ml of water, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was concentrated under reduced pressure, and aqueous saturated ammonium chloride was added to the residue, then extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol/aqueous ammonia=90/10/1) to obtain the entitled compound as an oily substance.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure, and aqueous saturated ammonium chloride
  4. additionwas added to the residue
  5. extractionextracted with chloroform
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified
  9. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol/aqueous ammonia=90/10/1)
  10. customto obtain the entitled compound as an oily substance

Sources & evidence

ORD record
ord-9e2823e718674544ad339e9acb947a5f
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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