Water → 3-[2-(2-Carbamoylhydrazonocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276948Notes

Reaction equation

HRID 276948 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)=[N:9]1.Cl.[NH2:31][NH:32][C:33]([NH2:35])=[O:34].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[C:33]([NH:32][N:31]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)=[N:9]1)(=[O:34])[NH2:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11236Semicarbazide hydrochlorideHCID 11430Potassium CarbonateHCID 110690413-[2-(2-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 573214913-[2-(2-Carbamoylhydrazonocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[2-(2-oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (231 mg), semicarbazide hydrochloride (101 mg), potassium carbonate (125 mg), water (2 ml), and ethanol (10 ml) was heated under reflux for 4 hours. Ethanol was evaporated in vacuo and the residue was partitioned between dichloromethane (30 ml) and saturated aqueous sodium bicarbonate (30 ml). After an additional extraction with dichloromethane, the combined extracts were washed with brine (20 ml), dried over anhydrous sodium sulfate, and evaporated in vacuo to give colorless crystals of 3-[2-(2-carbamoylhydrazonocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (125.8 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customEthanol was evaporated in vacuo
  4. customthe residue was partitioned between dichloromethane (30 ml) and saturated aqueous sodium bicarbonate (30 ml)
  5. extractionAfter an additional extraction with dichloromethane
  6. washthe combined extracts were washed with brine (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-72ef9bf54f214342b0c6cd0842442f24
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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