Phenylhydrazine → HCID 58072281, compound

HRID 2089926Notes

Reaction equation

HRID 2089926 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17](=O)[CH:18]=[CH:19][N:20](C)C)=[N:11]2)=[CH:6][CH:5]=1.[C:25]1([NH:31]N)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17]3[N:31]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:20]=[CH:19][CH:18]=3)=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 66710766HCID 66710766, compound

Product 1

HCID 58072281HCID 58072281, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(difluoromethoxy)phenyl]-3-[3-(dimethylamino)prop-2-enoyl]pyridazin-4(1H)-one (crude 747 mg, 2.22 mmol) in 20 mL of methanol was added phenylhydrazine (360 mg, 3.33 mmol). The mixture was refluxed for 4 h and concentrated. The residue was dissolved in dichloromethane (20 mL), washed with 1N HCl aqueous solution and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 1-[4-(difluoromethoxy)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (190 mg, 22% for two steps) as a yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  4. washwashed with 1N HCl aqueous solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-f3a2e67323aa48f3a809546d998ac9b6
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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