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

HRID 412368Notes

Reaction equation

HRID 412368 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[CH:14]1([C:20]([OH:22])=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl.Cl.[NH2:25][C:26]1[CH:58]=[CH:57][C:29]([O:30][C:31]2[CH:32]=[CH:33][C:34]3[N:38]=[C:37]([CH2:39][O:40][C:41]4[CH:54]=[CH:53][C:44]([CH2:45][CH:46]5[S:50][C:49](=[O:51])[NH:48][C:47]5=[O:52])=[CH:43][CH:42]=4)[N:36]([CH3:55])[C:35]=3[CH:56]=2)=[CH:28][CH:27]=1>CN(C)C=O>[O:51]=[C:49]1[NH:48][C:47](=[O:52])[CH:46]([CH2:45][C:44]2[CH:43]=[CH:42][C:41]([O:40][CH2:39][C:37]3[N:36]([CH3:55])[C:35]4[CH:56]=[C:31]([O:30][C:29]5[CH:57]=[CH:58][C:26]([NH:25][C:20]([CH:14]6[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]6)=[O:22])=[CH:27][CH:28]=5)[CH:32]=[CH:33][C:34]=4[N:38]=3)=[CH:54][CH:53]=2)[S:50]1

Participants

6

Reactant 4

HCID 7413Cyclohexanecarboxylic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 18537678N-[4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.32 ml) and ethyl chloroformate (0.08 ml) were added dropwise to a solution of cyclohexanecarboxylic acid (0.09 ml) in anhydrous N,N-dimethylformamide (8 ml). After stirring the mixture for 90 minutes, 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) was added and this mixture was stirred at room temperature for 2 hours and then for 90 minutes in an oil bath at 50° C. 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. The residue was recrystallized from ethyl acetate to afford the title compound (262 mg, pale orange powder, mp 182-184° C.).

Workup

  1. stirringthis mixture was stirred at room temperature for 2 hours
  2. waitfor 90 minutes in an oil bath at 50° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-468d6aaadaf146178730ef4b2c164dc8
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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