Acetic Anhydride → 1-(2-(5-(4-(methylsulfonyl)phenoxy)-2-(pyridin-2-yl)-1H-benzo[d]imidazol-6-yl)pyrrolidin-1-yl)ethanone

HRID 13278Notes

Reaction equation

HRID 13278 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][S:9]([C:12]1[CH:38]=[CH:37][C:15]([O:16][C:17]2[C:31]([CH:32]3[CH2:36][CH2:35][CH2:34][NH:33]3)=[CH:30][C:20]3[NH:21][C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[N:23][C:19]=3[CH:18]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C(Cl)Cl>[CH3:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[C:31]([CH:32]3[CH2:36][CH2:35][CH2:34][N:33]3[C:1](=[O:3])[CH3:2])=[CH:30][C:20]3[NH:21][C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[N:23][C:19]=3[CH:18]=2)=[CH:37][CH:38]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 231451755-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 111790251-(2-(5-(4-(methylsulfonyl)phenoxy)-2-(pyridin-2-yl)-1H-benzo[d]imidazol-6-yl)pyrrolidin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.003 ml of acetic anhydride was added to a methylene chloride (1 ml) solution of 10 mg of 5-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole, and the reaction liquid was stirred at room temperature for 1 hour. The reaction 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 white solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction solvent was evaporated away under reduced pressure
  3. customthe resulting residue was purified
  4. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-da68c63e5eb6410e8bc8a884065b8ba5
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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