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

HRID 242264ノート

反応式

HRID 242264 の反応式
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

参加物

8

反応物 5

HCID 313Hydrochloric Acid2 回HCID 6422Trifluoroacetic acidHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 10942334Sodium MethoxideHCID 66726233Ethyl 3-(dimethylamino)-2-(1H-1,2,3-triazol-1-yl)acrylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fec8a750eb1e4b5da08aaa15595034f2
出典データセット
uspto-grants-2014_02
特許番号
US08653111B2

反応ノート

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