Water → HCID 67455690, compound

HRID 2389293Notes

Reaction equation

HRID 2389293 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[CH3:10][NH:11][CH2:12][CH2:13][CH3:14].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH3:10][N:11]([CH2:12][CH2:13][CH3:14])[C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

8

Reactant 6

HCID 962WaterHCID 10472-Pyrazinecarboxylic acidHCID 12315N-MethylpropylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67455690HCID 67455690, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrazine carboxylic acid (1.00 g, 8.06 mmol) was dissolved in DMF (5 mL), and methylpropylamine (99 μL, 9.69 mmol), WSC.HCl (1.85 g, 9.69 mmol), and HOBt.H2O (1.48 g, 9.69 mmol) were added thereto, and then, the mixture was stirred at room temperature for 1 hour. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50) to give N-methyl-N-propylpyrazinecarboxamide (1.41 g, 7.86 mmol, yield: 98%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-f5727239cbe94bfda1ef9926da59cb97
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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