Methanol → HCID 58072476, compound

HRID 2089939Notes

Reaction equation

HRID 2089939 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:18]=[CH:17]C(=O)[C:15]([C:20](=O)[CH:21]=[CH:22][N:23](C)C)=[N:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27]1([NH:33]N)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:35][OH:36]>>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:18]=[CH:17][C:35](=[O:36])[C:15]([C:20]4[N:33]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:23]=[CH:22][CH:21]=4)=[N:14]3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 887MethanolHCID 7516PhenylhydrazineHCID 66710424HCID 66710424, compound

Product 1

HCID 58072476HCID 58072476, compoundYield 30%

Procedure

To a solution of 1-(4-cyclohexylphenyl)-3-[3-(dimethylamino)prop-2-enoyl]pyridazin-4(1H)-one (crude, 500 mg, 1.42 mmol) in 20 mL of methanol was added phenylhydrazine (615 mg, 5.70 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-cyclohexylphenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (170 mg, 30% 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-f41e3fd3eafd47fdbb7a7810f1f73b45
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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