Triethylamine → HCID 18537650, compound

HRID 412344

Reaction equation

HRID 412344 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([CH2:16][O:17][C:18]3[CH:31]=[CH:30][C:21]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:20][CH:19]=3)[N:13]([CH3:32])[C:12]=2[CH:33]=1.[C:37]12([N:47]=[C:48]=[O:49])[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2.C(N(CC)CC)C>CN(C)C=O>[C:37]12([NH:47][C:48]([NH:3][C:4]3[CH:36]=[CH:35][CH:34]=[C:6]([O:7][C:8]4[CH:9]=[CH:10][C:11]5[N:15]=[C:14]([CH2:16][O:17][C:18]6[CH:31]=[CH:30][C:21]([CH2:22][CH:23]7[S:27][C:26](=[O:28])[NH:25][C:24]7=[O:29])=[CH:20][CH:19]=6)[N:13]([CH3:32])[C:12]=5[CH:33]=4)[CH:5]=3)=[O:49])[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20599951-IsocyanatoadamantaneHCID 86587772HCID 86587772, compound

Product 1

HCID 18537650HCID 18537650, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[4-[6-(3-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), 1-adamantyl isocyanate (142 mg), triethylamine (153 mg) and anhydrous N,N-dimethylformamide (4 ml) was stirred at room temperature for 3 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 chromatographed on a silica gel column using ethyl acetate:n-hexane=3:1→4:1→ethyl acetate as the eluant. The product insoluble in methanol was isolated by filtration and further purified by preparative reverse phase high performance liquid chromatography using acetonitrile:water=50:50→60:40→65:35→70:30 as the eluant to afford the title compound (66 mg, mp 227.1-231.4° C.).

Workup

  1. concentrationThe reaction mixture was concentrated
  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
  7. customThe product insoluble in methanol was isolated by filtration
  8. customfurther purified by preparative reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-dcb08689d66241e6a7ac9dfcfe826b4d
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Linked notes

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