Hydrochloric Acid → 2-(6-Chloropyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

HRID 242264노트

반응식

HRID 242264 반응식
C(O[C:4](=[O:15])[C:5]([N:10]1[CH:14]=[CH:13][N:12]=[N:11]1)=[CH:6][N:7](C)C)C.[Cl:16][C:17]1[CH:22]=[C:21]([NH:23]N)[N:20]=[CH:19][N:18]=1.C(O)(C(F)(F)F)=O.Cl.C[O-].[Na+]>O1CCOCC1.C(O)C>[ClH:16].[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([N:23]2[C:4](=[O:15])[C:5]([N:10]3[CH:14]=[CH:13][N:12]=[N:11]3)=[CH:6][NH:7]2)[CH:22]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric Acid2회HCID 6422Trifluoroacetic acidHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 10942334Sodium MethoxideHCID 66726233Ethyl 3-(dimethylamino)-2-(1H-1,2,3-triazol-1-yl)acrylate

생성물 1

HCID 866352542-(6-Chloropyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 312751,4-Dioxane용매

실험 절차

10.0 g (47.7 mmol) of the compound from Example 3A and 8.3 g (57.1 mmol) of the compound from Example 7A are initially introduced into 100 ml ethanol and 1.5 ml (2.2 g, 19.0 mmol) TFA are added. The mixture is stirred under reflux for 12 h. A 4 M solution of hydrogen chloride in dioxane is then added in excess to the cooled reaction mixture, the mixture is extracted by stirring for approx. 1 h, the crystals which have precipitated out are filtered off and the residue on the filter is washed with dioxane and ethanol. The intermediate product obtained in this way is dissolved in 150 ml ethanol, 50 ml of a 25% strength methanolic sodium methylate solution are added and the mixture is stirred at RT for 2 h. The reaction mixture is then adjusted to pH 5 with 1 N hydrochloric acid and extracted by stirring at RT for a further 2 h, the solid is filtered off, the residue on the filter is washed with ethanol and the product is dried in vacuo.

후처리

  1. additionare added
  2. temperatureunder reflux for 12 h
  3. customexcess to the cooled reaction mixture
  4. extractionthe mixture is extracted
  5. stirringby stirring for approx. 1 h
  6. customthe crystals which have precipitated out
  7. filtrationare filtered off
  8. washthe residue on the filter is washed with dioxane and ethanol
  9. customThe intermediate product obtained in this way
  10. stirringthe mixture is stirred at RT for 2 h
  11. extractionextracted
  12. stirringby stirring at RT for a further 2 h
  13. filtrationthe solid is filtered off
  14. washthe residue on the filter is washed with ethanol
  15. customthe product is dried in vacuo

출처 및 근거

ORD 기록
ord-fec8a750eb1e4b5da08aaa15595034f2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653111B2

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