1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one → HCID 178493808, compound

HRID 1528078Notes

Reaction equation

HRID 1528078 reaction equation
C([N:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11](=[O:16])[C:10]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)=[N:9]1)C1C=CC=CC=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH3:15][O:14][C:12]1[C:11]([OH:16])=[C:10]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)[N:9]=[N:8][CH:13]=1

Participants

5

Reactant 1

HCID 680149051-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Product 1

HCID 178493808HCID 178493808, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (15.0 g) and palladium hydroxide on carbon (5.88 g, palladium 20%, moistened with 50% water) were suspended in THF (500 mL) and methanol (300 mL), and the suspension was stirred at room temperature for 2 days under a hydrogen atmosphere. The reaction mixture was filtered through celite, the filtrate was concentrated. The residue was solidified with ethanol/hexane to give the title compound (9.10 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ef39be397d644745b9beaea2ba26f2f3
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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