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Potassium Carbonate → 5-Tert-butyl-2-[3-(4-chlorobenzoyl)benzyl]-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one

HRID 1291296
Notes
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Reaction equation

HRID 1291296 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[N:13][NH:14][C:8]=2[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH2:25]Br)=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]2=[CH:12][N:13]([CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([C:20](=[O:21])[C:19]4[CH:30]=[CH:31][C:16]([Cl:15])=[CH:17][CH:18]=4)[CH:23]=3)[N:14]=[C:8]2[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 136496533-(4-Chlorobenzoyl)benzyl bromideHCID 189191095-Tert-butyl-1H-pyrazolo[3,4-d]pyridazin-4(5H)-one

Product 1

HCID 699592805-Tert-butyl-2-[3-(4-chlorobenzoyl)benzyl]-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (5 ml) was dissolved 5-t-butyl-1H-pyrazolo-[3,4-d]pyridazin-4(5H)-one (288 mg) followed by addition of 3-(4-chlorobenzoyl)benzyl bromide (712 mg) and potassium carbonate (318 mg), and the mixture was stirred at room temperature for 15 hours. This reaction mixture was extracted with ethyl acetate and the organic layer was serially washed with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=1:1), washed with the following solvent, and dried. As the washing solvent, diethyl ether was used for 5-t-butyl-1-[3-(4-chlorobenzoyl) benzyl]-1H-pyrazolo[3,4-d]pyridazin-4(5H)-one and n-hexane-diethyl ester was used for 5-t-butyl-2-[3-(4-chlorobenzoyl)benzyl]-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one.

Workup

  1. extractionThis reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was serially washed with water and saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=1:1)
  6. washwashed with the following solvent
  7. customdried

Sources & evidence

ORD record
ord-a31aea889c554d498c12aca2ecbd3c5f
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753664

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes