Dimethyl Sulfoxide → 1-(1-(6-(4-Methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanone

HRID 13365Notes

Reaction equation

HRID 13365 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][S:12]([C:15]1[CH:44]=[CH:43][C:18]([O:19][C:20]2[C:21]([N:35]3[CH2:39][CH2:38][CH2:37][CH:36]3[CH:40]([OH:42])[CH3:41])=[CH:22][C:23]3[NH:27][C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[N:25][C:24]=3[CH:34]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13].[Cl-].[NH4+]>C(N(CC)CC)C.C(Cl)Cl>[CH3:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:19][C:20]2[C:21]([N:35]3[CH2:39][CH2:38][CH2:37][CH:36]3[C:40](=[O:42])[CH3:41])=[CH:22][C:23]3[NH:27][C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[N:25][C:24]=3[CH:34]=2)=[CH:43][CH:44]=1)(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 231453781-(1-(6-(4-Methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanol

Product 1

HCID 113520131-(1-(6-(4-Methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

0.080 ml of oxalyl chloride and 0.087 ml of dimethylsulfoxide were added in order to 3 ml of methylene chloride at −78° C., and the reaction liquid was stirred at −78° C. for 10 minutes, and then a methylene chloride (2 ml) solution of 146 mg of the diastereomer mixture of 1-(1-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanol obtained in Examples 354 and 355, at −78° C. The reaction liquid was stirred at −78° C. for 30 minutes, and 0.42 ml of triethylamine was added to it, and the reaction mixture was stirred at −78° C. for 10 minutes, and then heated up to room temperature. Aqueous saturated ammonium chloride was added to the reaction liquid, extracted with ethyl acetate, 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=10/1) to obtain the entitled compound as a pale yellow solid.

Workup

  1. customthe reaction liquid
  2. customat −78° C
  3. customThe reaction liquid
  4. stirringwas stirred at −78° C. for 30 minutes
  5. stirringthe reaction mixture was stirred at −78° C. for 10 minutes
  6. temperatureheated up to room temperature
  7. extractionextracted with ethyl acetate
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. customthe resulting residue was purified
  11. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-470b1f592ac8402c86b33a2a603347c2
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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