Methylamine → 1H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-(2-pyridinyl)-

HRID 280449Notes

Reaction equation

HRID 280449 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[CH:5][C:4]=1[C:14]([O:16]CC)=O)#[N:2].[CH3:19][NH2:20]>CN(C=O)C>[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[CH:5][C:4]=1[C:14]([NH:20][CH3:19])=[O:16])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13654086ethyl 5-cyano-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

Product 1

HCID 1757841H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-(2-pyridinyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.5 g of 5-cyano-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester in 20 ml of DMF was added an excess of 40% aqueous monomethylamine so as not to precipitate out the pyrazole starting material. Approximately 24 hours later additional monomethylamine was added to the reaction mixture as well as additional DMF so as to keep these reactants in solution. The reaction mixture was heated and subsequently added to 150 ml of ice water. The precipitated solid was collected by filtration and recrystallized from methanol to afford 1.2 g of 5-cyano-1-(2-pyridinyl)-N-methyl-1H-pyrazole-4-carboxamide. MP=200°-202° C.

Workup

  1. customto precipitate out the pyrazole starting material
  2. additionApproximately 24 hours later additional monomethylamine was added to the reaction mixture as well as additional DMF so as
  3. temperatureThe reaction mixture was heated
  4. additionsubsequently added to 150 ml of ice water
  5. filtrationThe precipitated solid was collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-64f4ac693f6c4871b6899d7e31caf0bc
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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