Hydrochloric Acid → 2-Pyridin-2-yl-4-(6-trifluormethylpyridin-3-yl)-1,2-dihydro-3h-pyrazol-3-one

HRID 1526089Notes

Reaction equation

HRID 1526089 reaction equation
C(O[C:4](=[O:18])[C:5]([C:8]1[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1)=[CH:6]O)C.[NH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[NH2:20].C([O-])C.[Na+].Cl>C(O)C>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:19]1[C:4](=[O:18])[C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)=[CH:6][NH:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 786452-HydrazinopyridineHCID 2723922Sodium ethoxideHCID 687048893-Hydroxy-2-(6-trifluoromethylpyridin-3-yl)-acrylic acid ethyl ester

Product 1

HCID 591869752-Pyridin-2-yl-4-(6-trifluormethylpyridin-3-yl)-1,2-dihydro-3h-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

261 mg (1.00 mmol) of the compound from Example 41A and 115 mg (1.05 mmol) 2-hydrazinopyridine are dissolved in 5 ml anhydrous ethanol under argon and the mixture is stirred at RT for 20 h. 68 mg (1.00 mmol) sodium ethanolate are added, the mixture is stirred at RT for 30 min and 1 M hydrochloric acid and a little ethanol are then added, a precipitate separating out. This is filtered off, washed with a little ethanol and dried in vacuo.

Workup

  1. stirringthe mixture is stirred at RT for 30 min
  2. customa precipitate separating out
  3. filtrationThis is filtered off
  4. washwashed with a little ethanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e6e2cc5e18654ff9b82927e2656b93b3
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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