Triethylamine → HCID 18537676, compound

HRID 412361Notes

Reaction equation

HRID 412361 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH2:25][O:26][C:27]4[CH:40]=[CH:39][C:30]([CH2:31][CH:32]5[S:36][C:35](=[O:37])[NH:34][C:33]5=[O:38])=[CH:29][CH:28]=4)[N:22]([CH3:41])[C:21]=3[CH:42]=2)[CH:7]=[CH:8][C:9]=1[C:10]([CH3:13])([CH3:12])[CH3:11].[F:43][C:44]([F:55])([F:54])[C:45]1[CH:50]=[CH:49][C:48]([N:51]=[C:52]=[O:53])=[CH:47][CH:46]=1.C(N(CC)CC)C>CN(C)C=O>[C:10]([C:9]1[CH:8]=[CH:7][C:6]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH2:25][O:26][C:27]4[CH:40]=[CH:39][C:30]([CH2:31][CH:32]5[S:36][C:35](=[O:37])[NH:34][C:33]5=[O:38])=[CH:29][CH:28]=4)[N:22]([CH3:41])[C:21]=3[CH:42]=2)=[CH:5][C:4]=1[NH:3][C:52]([NH:51][C:48]1[CH:47]=[CH:46][C:45]([C:44]([F:43])([F:54])[F:55])=[CH:50][CH:49]=1)=[O:53])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 86587776HCID 86587776, compound

Product 1

HCID 18537676HCID 18537676, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[4-[6-[2-(3-amino-4-t-butylphenyl)ethoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.40 g), α,α,α-trifluoro-p-tolyl isocyanate (0.13 g), triethylamine (0.13 g) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 24 hours and then at 60° C. for 2.5 hours. The reaction mixture was concentrated and 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 purified by preparative reverse phase high performance liquid chromatography using acetonitrile:water=57:43 containing triethylamine (2%) and acetic acid (2%) as the eluant to afford the title compound (0.24 g, mp 165-167° C.).

Workup

  1. waitat 60° C. for 2.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by preparative reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-8109f694fde940d793168f51b2ba6b10
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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