2-(Methylthio)benzimidazole → 1-{[2-(methylthio)-1H-benzimidazol-1-yl]methyl}-4-propylpyrrolidin-2-one

HRID 1295817

Reaction equation

HRID 1295817 reaction equation
C(N(CC)C(=O)O[CH2:6][N:7]1[CH2:11][CH:10]([CH2:12][CH2:13][CH3:14])[CH2:9][C:8]1=[O:15])C.[CH3:19][S:20][C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1>C(#N)C>[CH3:19][S:20][C:21]1[N:22]([CH2:6][N:7]2[CH2:11][CH:10]([CH2:12][CH2:13][CH3:14])[CH2:9][C:8]2=[O:15])[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1

Participants

4

Reactant 2

HCID 235392-(Methylthio)benzimidazoleHCID 11448237(2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

Product 1

HCID 111508421-{[2-(methylthio)-1H-benzimidazol-1-yl]methyl}-4-propylpyrrolidin-2-oneYield 40.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2-oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate a26 (1 eq, 3.18 mmol, 0.5 g) and 2-(methylthio)-benzimidazole (1.25 eq, 3.90 mmol, 0.64 g) in acetonitrile (4 ml) was heated under reflux for 42 h. The solvent was evaporated under reduce pressure and purification by preparative chromatography on reverse phase afforded 390 mg of 1-{[2-(methylthio)-1H-benzimidazol-1-yl]methyl}-4-propylpyrrolidin-2-one 90 (HPLC purity (U.V.): 85%; Yield: 40.3%).

Workup

  1. temperatureunder reflux for 42 h
  2. customThe solvent was evaporated
  3. custompressure and purification by preparative chromatography on reverse phase

Sources & evidence

ORD record
ord-ec4a7afc21ab4e00a3bd9ec8f4ba32d4
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Linked notes

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