Potassium Iodide → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butylthio}acetic Acid Methyl Ester

HRID 1271298Notes

Reaction equation

HRID 1271298 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:11]=1)[CH:7]([CH3:9])[CH3:8].[C:28]([O:32][CH3:33])(=[O:31])[CH2:29][SH:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:33][O:32][C:28](=[O:31])[CH2:29][S:30][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:11]=1)[CH:7]([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 184526331-bromo-4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butane

Product 1

HCID 693549872-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butylthio}acetic Acid Methyl EsterYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.17 g of 1-bromo-4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butane, 0.29 g of methyl thioglycolate, 0.46 g of potassium carbonate, a catalytic amount of potassium iodide and 27 ml of acetonitrile were mixed and the mixture was refluxed for 4 hours. The insoluble matter was removed by filtration and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.19 g of the desired compound as a pale yellow crystal having a melting point of 64 to 67° C.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe insoluble matter was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c45c2e87adad4e048ee59e42e4f4f7cd
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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