Citric Acid → 2-(3-Bromo-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethylcarbamoyl)indole-1-acetic acid

HRID 963056Notes

Reaction equation

HRID 963056 reaction equation
[Br:1][C:2]1[N:6]([C:7]2[S:8][C:9]([CH2:21][CH3:22])=[CH:10][C:11]=2[C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:5]([CH2:23][NH:24][C:25]([C:27]2[N:28]([CH2:36][C:37]([O:39]CC)=[O:38])[C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[N:4][N:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[Br:1][C:2]1[N:6]([C:7]2[S:8][C:9]([CH2:21][CH3:22])=[CH:10][C:11]=2[C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:5]([CH2:23][NH:24][C:25]([C:27]2[N:28]([CH2:36][C:37]([OH:39])=[O:38])[C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 67727711Ethyl 2-(3-bromo-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethylcarbamoyl)indole-1-acetate

Product 1

HCID 677277782-(3-Bromo-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethylcarbamoyl)indole-1-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(3-bromo-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethylcarbamoyl)indole-1-acetate and a 2M aqueous sodium hydroxide solution are added to ethanol, and the mixture is refluxed with stirring for 1 hour. An aqueous citric acid solution is added to adjust the reaction mixture to pH 3 to give 2-(3-bromo-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethylcarbamoyl)indole-1-acetic acid.

Workup

  1. temperaturethe mixture is refluxed

Sources & evidence

ORD record
ord-71b930e5bd6a4371ba11ac4d9099392d
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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