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

HRID 1753828Notes

Reaction equation

HRID 1753828 reaction equation
C(O)(C(F)(F)F)=O.C(O[C:11](=[O:22])[C:12]([N:17]1[CH:21]=[CH:20][N:19]=[N:18]1)=[CH:13][N:14](C)C)C.[Cl:23][C:24]1[CH:29]=[C:28]([NH:30]N)[N:27]=[CH:26][N:25]=1>C(O)C>[ClH:23].[Cl:23][C:24]1[N:25]=[CH:26][N:27]=[C:28]([N:30]2[C:11](=[O:22])[C:12]([N:17]3[CH:21]=[CH:20][N:19]=[N:18]3)=[CH:13][NH:14]2)[CH:29]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 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 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

1.1 ml (1.6 g, 13.8 mmol) TFA are added to a mixture of 7.3 g (34.6 mmol) of the compound from Example 3A and 6.0 g (41.5 mmol) of the compound from Example 7A in 70 ml ethanol and the mixture is stirred at 100° C. for 20 h. The solid which has precipitated out is filtered off and the filtrate is concentrated in vacuo. The residue is suspended in 100 ml ethanol, 30 ml of a 30% strength sodium methanolate solution in methanol are added and the mixture is stirred at RT for 1.5 h. After addition of 42 ml of a 4 N solution of hydrogen chloride in dioxane (pH=5-6) and after stirring for 30 min, the solid is filtered off, washed first with ethanol and then with diethyl ether and dried in vacuo. Further purification is carried out by stirring in ethanol and acetonitrile several times. 10 ml of a 4 N solution of hydrogen chloride in dioxane are then added and the mixture is stirred at RT for 16 h. The product is filtered off, washed first with acetonitrile and then with diethyl ether and dried in vacuo.

Workup

  1. customThe solid which has precipitated out
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated in vacuo
  4. addition30 ml of a 30% strength sodium methanolate solution in methanol are added
  5. stirringthe mixture is stirred at RT for 1.5 h
  6. additionAfter addition of 42 ml of a 4 N solution of hydrogen chloride in dioxane (pH=5-6)
  7. stirringafter stirring for 30 min
  8. filtrationthe solid is filtered off
  9. washwashed first with ethanol
  10. dry with materialwith diethyl ether and dried in vacuo
  11. customFurther purification
  12. stirringby stirring in ethanol
  13. addition10 ml of a 4 N solution of hydrogen chloride in dioxane are then added
  14. stirringthe mixture is stirred at RT for 16 h
  15. filtrationThe product is filtered off
  16. washwashed first with acetonitrile
  17. dry with materialwith diethyl ether and dried in vacuo

Sources & evidence

ORD record
ord-b6428e6b615b453c9944cc60d97c36ad
Source dataset
uspto-grants-2015_10
Patent number
US09168249B2

Reaction notes

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