Methanol → 1-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333754Notes

Reaction equation

HRID 333754 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.[H-].[Na+].Br[CH:24]1[CH2:27][CH2:26][CH2:25]1.CO>CN(C=O)C>[CH:24]1([N:7]2[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[O:20])[C:5]([C:9]3[N:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:12]=[CH:11][CH:10]=3)=[N:6]2)[CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 78110BromocyclobutaneHCID 178493808HCID 178493808, compound

Product 1

HCID 680148321-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, to a solution of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (2.0 g) in DMF (40 mL) was added under ice-cooling 60% sodium hydride (596 mg), and the mixture was stirred for 1.5 hr. Then, bromocyclobutane (1.05 mL) was added, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added methanol, and the mixture was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) and further purified by HPLC to give the title compound (0.92 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)
  4. customfurther purified by HPLC

Sources & evidence

ORD record
ord-ca8fdac5af4d41638999cf49f470c858
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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