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

HRID 242265Notes

Reaction equation

HRID 242265 reaction equation
C(O[C:4](=[O:15])[C:5]([N:10]1[CH:14]=[CH:13][N:12]=[CH: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>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]=[CH:11]3)=[CH:6][NH:7]2)[CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 66726242Ethyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylate

Product 1

HCID 866352552-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 g (47.8 mmol) of the compound from Example 42A and 8.3 g (57.3 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. The crystals which have precipitated out are filtered off, the residue on the filter is rinsed with ethanol and the intermediate product is dried overnight in vacuo. This is then suspended in 20 ml methanol, 100 ml of a 4 M solution of hydrogen chloride in dioxane are added and the mixture is subsequently stirred at RT for 1 h. The solid is filtered off, the residue on the filter is washed with dioxane, ethyl acetate and diisopropyl ether and the product is dried in vacuo.

Workup

  1. additionare added
  2. temperatureunder reflux for 12 h
  3. customThe crystals which have precipitated out
  4. filtrationare filtered off
  5. washthe residue on the filter is rinsed with ethanol
  6. customthe intermediate product is dried overnight in vacuo
  7. addition100 ml of a 4 M solution of hydrogen chloride in dioxane are added
  8. stirringthe mixture is subsequently stirred at RT for 1 h
  9. filtrationThe solid is filtered off
  10. washthe residue on the filter is washed with dioxane, ethyl acetate and diisopropyl ether
  11. customthe product is dried in vacuo

Sources & evidence

ORD record
ord-4c9b00ab5ad14b829b1ff5ca37894509
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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