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

HRID 1249435노트

반응식

HRID 1249435 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2.5 g of 5cyano-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.

후처리

  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

출처 및 근거

ORD 기록
ord-240368c3093e4587be438cc601a236f0
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04631343

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