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

HRID 242264Notes

Reaction equation

HRID 242264 reaction equation
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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fec8a750eb1e4b5da08aaa15595034f2
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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