Potassium Carbonate → HCID 69961365, compound

HRID 1291297Notes

Reaction equation

HRID 1291297 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]=[C:30]([Cl:32])[CH:29]=[CH:28][C:17]=1[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)=[O:19].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]([CH2:24][C:23]3[CH:22]=[CH:21][C:20]([C:18](=[O:19])[C:17]4[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:16]=4[Cl:15])=[CH:27][CH:26]=3)[N:14]=[C:8]2[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18919109HCID 18919109, compoundHCID 189192794-(2,4-Dichlorobenzoyl)benzyl bromide

Product 1

HCID 69961365HCID 69961365, compound

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 4-(2,4-dichlorobenzoyl)benzyl bromide (791 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-hexaneethyl acetate=1:1). Then, 5-t-butyl-2-[4-(2,4-dichlorobenzoyl)benzyl]-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one was washed with n-hexane-diethyl ether and dried.

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-hexaneethyl acetate=1:1)
  6. washThen, 5-t-butyl-2-[4-(2,4-dichlorobenzoyl)benzyl]-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one was washed with n-hexane-diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-f19db99f8abf419f945e65773f60d1bd
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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