Dimethylformamide → HCID 54080259, compound

HRID 2287600Notes

Reaction equation

HRID 2287600 reaction equation
[CH3:1][C:2]1[C:20]([N:21]([C:23](=[O:40])[CH2:24][NH:25][C:26](=[O:39])[CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:38])[NH:36][CH3:37])=[CH:31][CH:30]=2)[CH3:22])=[CH:19][CH:18]=[C:17]([CH3:41])[C:3]=1[CH2:4][O:5][C:6]1[C:14]2[N:13]=[C:12]([SH:15])[N:11]([CH3:16])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[C:42](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[CH3:1][C:2]1[C:20]([N:21]([C:23](=[O:40])[CH2:24][NH:25][C:26](=[O:39])[CH:27]=[CH:28][C:29]2[CH:30]=[CH:31][C:32]([C:35](=[O:38])[NH:36][CH3:37])=[CH:33][CH:34]=2)[CH3:22])=[CH:19][CH:18]=[C:17]([CH3:41])[C:3]=1[CH2:4][O:5][C:6]1[C:14]2[N:13]=[C:12]([S:15][CH3:42])[N:11]([CH3:16])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178485329HCID 178485329, compound

Product 1

HCID 54080259HCID 54080259, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[2,6-dimethyl-3-[N-(4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-mercapto-1-methyl-1H-benzimidazole (34.9 mg), potassium carbonate (10.1 mg) and N,N-dimethylformamide (0.4 ml) was added methyl iodide (4 μl) at ambient temperature, and the mixture was stirred for 16 hours. The reaction mixture was poured into water, and extracted with chloroform. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (ethyl acetate:methanol=10:1, v/v) to give 4-[2,6-dimethyl-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-1-methyl-2-methylthio-1H-benzimidazole (21.2 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (ethyl acetate

Sources & evidence

ORD record
ord-36258b0e1f48433f989793dea0b784cc
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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