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

HRID 13277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 13277
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]=[CH: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:34]=[CH:33][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]=[CH:27][CH:26]=[CH:25][N:24]=4)=[N:20][C:19]=3[CH:29]=2)=[CH:37][CH:36]=1)(=[O:39])=[O:40]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 231457212,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Produkt 1

HCID 231451755-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

500 mg of potassium carbonate was added to a solution of 375 mg of 2,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone in a mixture of 16 ml of methanol and 3 ml of water, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was distilled under reduced pressure, diluted with aqueous saturated sodium bicarbonate added thereto, and then extracted with ethyl acetate. The organic layer was washed with saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol/aqueous ammonia=10/1/0.1) to obtain the entitled compound as a pale yellow solid.

Aufarbeitung

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. distillationwas distilled under reduced pressure
  4. additiondiluted with aqueous saturated sodium bicarbonate
  5. additionadded
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated saline
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol/aqueous ammonia=10/1/0.1)

Quellen und Nachweise

ORD-Eintrag
ord-b545d142e5504e30a1a6cdd0495f598b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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