Triethylamine → N-[4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]cyclopentanecarboxamide

HRID 2303835Notes

Reaction equation

HRID 2303835 reaction equation
ClC(OCC)=O.[CH:7]1([C:12]([OH:14])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C.Cl.Cl.[NH2:24][C:25]1[CH:57]=[CH:56][C:28]([O:29][C:30]2[CH:31]=[CH:32][C:33]3[N:37]=[C:36]([CH2:38][O:39][C:40]4[CH:53]=[CH:52][C:43]([CH2:44][CH:45]5[S:49][C:48](=[O:50])[NH:47][C:46]5=[O:51])=[CH:42][CH:41]=4)[N:35]([CH3:54])[C:34]=3[CH:55]=2)=[CH:27][CH:26]=1>CN(C)C=O.O>[CH:7]1([C:12]([NH:24][C:25]2[CH:57]=[CH:56][C:28]([O:29][C:30]3[CH:31]=[CH:32][C:33]4[N:37]=[C:36]([CH2:38][O:39][C:40]5[CH:53]=[CH:52][C:43]([CH2:44][CH:45]6[S:49][C:48](=[O:50])[NH:47][C:46]6=[O:51])=[CH:42][CH:41]=5)[N:35]([CH3:54])[C:34]=4[CH:55]=3)=[CH:27][CH:26]=2)=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18840Cyclopentanecarboxylic acidHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 10210059N-[4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]cyclopentanecarboxamideYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl chloroformate (87 mg) was added dropwise to a solution of cyclopentanecarboxylic acid (90 mg) and triethylamine (232 mg) in anhydrous N,N-dimethylformamide (8 ml) at ambient temperature. The mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture was added 5-{4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione dihydrochloride (400 mg) in small portions. The mixture was stirred at ambient temperature for 5 hours and allowed to stand at the same temperature overnight. After concentration of the mixture, water was added to the reaction mixture and the insoluble product was isolated by filtration and washed with water and ethyl acetate to give the title compound (236 mg).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 5 hours
  2. customto stand at the same temperature overnight
  3. customthe insoluble product was isolated by filtration
  4. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-c3694f10ec134c1b9d70062f5dab9234
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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