Triethylamine → HCID 18537619, compound

HRID 412367Notes

Reaction equation

HRID 412367 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12].Cl.Cl.[NH2:21][C:22]1[CH:54]=[CH:53][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]3[N:34]=[C:33]([CH2:35][O:36][C:37]4[CH:50]=[CH:49][C:40]([CH2:41][CH:42]5[S:46][C:45](=[O:47])[NH:44][C:43]5=[O:48])=[CH:39][CH:38]=4)[N:32]([CH3:51])[C:31]=3[CH:52]=2)=[CH:24][CH:23]=1>CN(C)C=O>[F:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:10]=1[C:11]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]3[N:34]=[C:33]([CH2:35][O:36][C:37]4[CH:38]=[CH:39][C:40]([CH2:41][CH:42]5[S:46][C:45](=[O:47])[NH:44][C:43]5=[O:48])=[CH:49][CH:50]=4)[N:32]([CH3:51])[C:31]=3[CH:52]=2)=[CH:53][CH:54]=1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5880812,4-Difluorobenzoyl chlorideHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 18537619HCID 18537619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction was conducted by a similar procedure to that described in Example 52 using triethylamine (0.32 ml), 2,4-difluorobenzoyl 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 and 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 chromatographed on a silica gel column using ethyl acetate:n-hexane=3:1 to afford the title compound (251 mg, white powder, mp 172-174° C.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned 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-d69562d7d62c45df8d7f72a746c482fa
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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