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Acetic Anhydride → 6-(Acetylpyrrolidin-2-yl)-5-(4-(2-methyl-2H-tetrazol-5-yl)phenoxy)-2-pyridin-2-yl-1H-benzimidazole

HRID 13406
Notes
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Reaction equation

HRID 13406 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][N:9]1[N:13]=[N:12][C:11]([C:14]2[CH:40]=[CH:39][C:17]([O:18][C:19]3[C:33]([CH:34]4[CH2:38][CH2:37][CH2:36][NH:35]4)=[CH:32][C:22]4[NH:23][C:24]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=5)=[N:25][C:21]=4[CH:20]=3)=[CH:16][CH:15]=2)=[N:10]1>C(Cl)(Cl)Cl>[C:1]([N:35]1[CH2:36][CH2:37][CH2:38][CH:34]1[C:33]1[C:19]([O:18][C:17]2[CH:16]=[CH:15][C:14]([C:11]3[N:12]=[N:13][N:9]([CH3:8])[N:10]=3)=[CH:40][CH:39]=2)=[CH:20][C:21]2[N:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[NH:23][C:22]=2[CH:32]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 231453565-(4-(2-methyl-2H-tetrazol-5-yl)phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 114090126-(Acetylpyrrolidin-2-yl)-5-(4-(2-methyl-2H-tetrazol-5-yl)phenoxy)-2-pyridin-2-yl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.007 ml of acetic anhydride was added to a chloroform (1 ml) solution of 30.9 mg of 5-(4-(2-methyl-2H-tetrazol-5-yl)phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole enantiomer B obtained in Example 542, and the reaction liquid was stirred at room temperature for 10 minutes. 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 one chiral form of the entitled compound as a white solid.

Workup

  1. customobtained in Example 542
  2. customthe reaction liquid
  3. customThe reaction solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-aeb0761e18e840ad9ac469085f1aadfe
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes