Dimethylformamide → HCID 54080259, compound

HRID 636524Notes

Reaction equation

HRID 636524 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-d5ac00db3c194e74ae3333f975682b4d
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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