Benzoyl chloride → 5-{4-[6-(4-Benzoylaminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione

HRID 412363Notes

Reaction equation

HRID 412363 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.Cl.[NH2:19][C:20]1[CH:52]=[CH:51][C:23]([O:24][C:25]2[CH:26]=[CH:27][C:28]3[N:32]=[C:31]([CH2:33][O:34][C:35]4[CH:48]=[CH:47][C:38]([CH2:39][CH:40]5[S:44][C:43](=[O:45])[NH:42][C:41]5=[O:46])=[CH:37][CH:36]=4)[N:30]([CH3:49])[C:29]=3[CH:50]=2)=[CH:22][CH:21]=1>CN(C)C=O>[O:45]=[C:43]1[NH:42][C:41](=[O:46])[CH:40]([CH2:39][C:38]2[CH:37]=[CH:36][C:35]([O:34][CH2:33][C:31]3[N:30]([CH3:49])[C:29]4[CH:50]=[C:25]([O:24][C:23]5[CH:51]=[CH:52][C:20]([NH:19][C:8](=[O:15])[C:9]6[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=6)=[CH:21][CH:22]=5)[CH:26]=[CH:27][C:28]=4[N:32]=3)=[CH:48][CH:47]=2)[S:44]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 185375725-{4-[6-(4-Benzoylaminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction was conducted by a similar procedure to that described in Example 52 using triethylamine (0.36 ml), benzoyl chloride (0.10 ml), 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) and anhydrous N,N-dimethylformamide (8 ml). 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 then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:1→2:1→3:1→4:1 as the eluant to afford the title compound (247 mg, white powder, mp 200-204° 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. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-3add40acc7d14567b843d59a4e352407
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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