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

HRID 13405Notes

Reaction equation

HRID 13405 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]

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

0.006 ml of acetic anhydride was added to a chloroform (1 ml) solution of 24.7 mg of 5-(4-(2-methyl-2H-tetrazol-5-yl)phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole enantiomer A 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. customA obtained 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-9a22161190b044088dc39b0a1440756e
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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