p-Toluenesulfonic acid → 2-(4,5-Dimethylpyridin-2-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

HRID 1913204Notes

Reaction equation

HRID 1913204 reaction equation
CN(C)[CH:3]=[C:4]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:5](OCC)=[O:6].[NH:17]([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([CH3:26])=[CH:21][N:20]=1)[NH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:25][C:23]1[C:22]([CH3:26])=[CH:21][N:20]=[C:19]([N:17]2[C:5](=[O:6])[C:4]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:3][NH:18]2)[CH:24]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 552791581154030-52-0HCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Product 1

HCID 592801902-(4,5-Dimethylpyridin-2-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

220 mg (1.0 mmol) of the compound from Example 2A are initially charged in 5 ml of ethanol. 137 mg (1.0 mmol) of the compound from Example 21A and 38 mg (0.2 mmol) of p-toluenesulfonic acid are added, and the mixture is stirred under reflux for 16 h. The mixture is then allowed to cool to RT, and the solid formed is filtered off, washed with tert-butyl methyl ether and dried under high vacuum. This gives 28 mg of the title compound. The mother liquor is put aside and used for preparing the hydrochloride (see Example 87).

Workup

  1. temperatureunder reflux for 16 h
  2. customthe solid formed
  3. filtrationis filtered off
  4. washwashed with tert-butyl methyl ether
  5. customdried under high vacuum
  6. customused for preparing the hydrochloride (see Example 87)

Sources & evidence

ORD record
ord-160c512f588e4d75a9c22877d81ae7f1
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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