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

HRID 412369Notes

Reaction equation

HRID 412369 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[CH:14]1([C:19]([OH:21])=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.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:50]=[C:48]1[NH:47][C:46](=[O:51])[CH:45]([CH2:44][C:43]2[CH:42]=[CH:41][C:40]([O:39][CH2:38][C:36]3[N:35]([CH3:54])[C:34]4[CH:55]=[C:30]([O:29][C:28]5[CH:56]=[CH:57][C:25]([NH:24][C:19]([CH:14]6[CH2:15][CH2:16][CH2:17][CH2:18]6)=[O:21])=[CH:26][CH:27]=5)[CH:31]=[CH:32][C:33]=4[N:37]=3)=[CH:53][CH:52]=2)[S:49]1

Participants

6

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]cyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction was conducted by a similar procedure to that described in Example 58 using triethylamine (0.32 ml), ethyl chloroformate (0.08 ml), cyclopentanecarboxylic acid (0.09 ml), anhydrous N,N-dimethylformamide (8 ml) and 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg). The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. To the residue was added water and ethyl acetate and the insoluble material was isolated by filtration to afford the title compound (236 mg, white powder, mp 227-228° C.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionTo the residue was added water and ethyl acetate
  7. customthe insoluble material was isolated by filtration

Sources & evidence

ORD record
ord-932a8b6aa20b4db6ae7f38a1ba222ad0
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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