Potassium Carbonate → 2-[4-(4-Chlorobenzoyl)benzyl]-3,5-dimethyl-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one

HRID 1291300Notes

Reaction equation

HRID 1291300 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[N:7]=[CH:6][C:5]=2[NH:4][N:3]=1.[Cl:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([C:20]2[CH:27]=[CH:26][C:23]([CH2:24][N:3]3[C:2]([CH3:1])=[C:10]4[C:5]([CH:6]=[N:7][N:8]([CH3:12])[C:9]4=[O:11])=[N:4]3)=[CH:22][CH:21]=2)=[O:19])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178434371HCID 178434371, compound

Product 1

HCID 699602892-[4-(4-Chlorobenzoyl)benzyl]-3,5-dimethyl-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (2 ml) was dissolved 3,5-dimethyl-1H-pyrazolo [3,4-d]pyridazin-4(5H)-one (94 mg) followed by addition of 4-(4-chlorobenzoyl)benzyl bromide (279 mg) and potassium carbonate (124 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=1:4), washed with the following solvent, and dried. As the washing solvent, n-hexanediethyl ether was used for 1-[4-(4-chlorobenzoyl) benzyl]-3,5-dimethyl-1H-pyrazolo[3,4-d]pyridazin-4(5H)-one and diethyl ether for 2-[4-(4-chlorobenzoyl)benzyl]-3,5-dimethyl-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=1:4)
  6. washwashed with the following solvent
  7. customdried

Sources & evidence

ORD record
ord-3cf81f9499824ebe8cd0dd859bfa2955
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…