p-Toluenesulfonic acid monohydrate → 2-[5-(2,2-Dimethylpropoxy)pyridin-2-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one

HRID 876706Notes

Reaction equation

HRID 876706 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.[CH3:16][C:17]([CH3:29])([CH3:28])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26]N)=[N:24][CH:25]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:16][C:17]([CH3:29])([CH3:28])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:4](=[O:15])[C:5]([N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)=[CH:6][NH:7]2)=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 552791605-(2,2-Dimethylpropoxy)-2-hydrazinopyridineHCID 66726242Ethyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylate

Product 1

HCID 596036952-[5-(2,2-Dimethylpropoxy)pyridin-2-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

233 mg (1.0 mmol, purity 90%) of the compound from Example 42A are initially introduced into 4 ml ethanol. 260 mg (1.0 mmol, purity 75%) of the compound from Example 12A and 38 mg (0.2 mmol) p-toluenesulfonic acid monohydrate are added and the mixture is stirred under reflux for 16 h. The mixture is then allowed to cool to RT, the solid which has precipitated out is filtered off and washed with a little ethanol and the solid is dried under a high vacuum. A further amount of the target compound is obtained by purifying the mother liquor of the filtration via preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA).

Workup

  1. temperatureunder reflux for 16 h
  2. customthe solid which has precipitated out
  3. filtrationis filtered off
  4. washwashed with a little ethanol
  5. customthe solid is dried under a high vacuum
  6. customA further amount of the target compound is obtained
  7. customby purifying
  8. filtrationthe mother liquor of the filtration
  9. additionvia preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)

Sources & evidence

ORD record
ord-aee146053c8d4d75b57b23f9690234ff
Source dataset
uspto-grants-2015_03
Patent number
US08987261B2

Reaction notes

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