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

HRID 562456Notes

Reaction equation

HRID 562456 reaction equation
CN(C)[CH:3]=[C:4]([N:10]1[CH:14]=[CH:13][N:12]=[N:11]1)[C:5](OCC)=[O:6].[Cl:16][C:17]1[CH:22]=[C:21]([NH:23][NH2:24])[N:20]=[CH:19][N:18]=1.FC(F)(F)C(O)=O.Cl.C[O-].[Na+]>C(O)C.O1CCOCC1>[ClH:16].[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([N:23]2[C:5](=[O:6])[C:4]([N:10]3[CH:14]=[CH:13][N:12]=[N:11]3)=[CH:3][NH:24]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 8A and 8.3 g (57.1 mmol) of the compound from Example 11A are initially charged in 100 ml of ethanol, and 1.5 ml (2.2 g, 19.0 mmol) of trifluoroacetic acid are added. The mixture is stirred under reflux for 12 h. An excess of a 4 M solution of hydrogen chloride in dioxane is then added to the cooled reaction mixture, the mixture is stirred for about 1 h, the precipitated crystals are filtered off and the filter residue is washed with dioxane and ethanol. The intermediate obtained in this manner is dissolved in 150 ml of ethanol, 50 ml of a 25% strength methanolic sodium methoxide solution are added and the mixture is stirred at RT for 2 h. The reaction mixture is then adjusted with 1 N hydrochloric acid to pH=5 and stirred at RT for a further 2 h, the solid is filtered off, the filter residue is washed with ethanol and the product is dried under reduced pressure. Yield: 7.0 g (49% of theory)

Workup

  1. temperatureunder reflux for 12 h
  2. stirringthe mixture is stirred for about 1 h
  3. filtrationthe precipitated crystals are filtered off
  4. washthe filter residue is washed with dioxane and ethanol
  5. customThe intermediate obtained in this manner
  6. stirringthe mixture is stirred at RT for 2 h
  7. stirringstirred at RT for a further 2 h
  8. filtrationthe solid is filtered off
  9. washthe filter residue is washed with ethanol
  10. customthe product is dried under reduced pressure

Sources & evidence

ORD record
ord-cdc501f838e94302b36da5de2c2f9ae9
Source dataset
uspto-grants-2011_11
Patent number
US08067407B2

Reaction notes

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