Potassium Carbonate → HCID 69959941, compound

HRID 1291299Notes

Reaction equation

HRID 1291299 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]2[C:12]([CH3:15])=[N:13][NH:14][C:8]=2[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]2=[C:12]([CH3:15])[N:13]([CH2:27][C:26]3[CH:25]=[CH:24][C:23]([C:21](=[O:22])[C:20]4[CH:31]=[CH:32][C:17]([F:16])=[CH:18][CH:19]=4)=[CH:30][CH:29]=3)[N:14]=[C:8]2[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 178434370HCID 178434370, compound

Product 1

HCID 69959941HCID 69959941, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml) was dissolved 5-t-butyl-3-methyl-1H-pyrazolo [3,4-d]pyridazin-4(5H)-one (516 mg) followed by addition of 4-(4-fluorobenzoyl)benzyl bromide (1.1 g) and potassium carbonate (525 mg), and the mixture was stirred at room temperature for 15 hours. This reaction mixture was extracted with diethyl ether 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), washed with the following solvent, and dried. As the washing solvent, n-hexanediethyl ether was used for 5-t-butyl-1-[4-(4-fluorobenzoyl) benzyl]-3-methyl-1H-pyrazolo[3,4-d]-pyridazin-4(5H)-one and diethyl ether-ethyl acetate for 5-t-butyl-2-[4-(4-fluorobenzoyl)benzyl]-3-methyl-2H-pyrazolo [3,4-d]pyridazin-4(5H)-one.

Workup

  1. extractionThis reaction mixture was extracted with diethyl ether
  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. washwashed with the following solvent
  7. customdried

Sources & evidence

ORD record
ord-1b71581e322e46779a22dd1ed42ddff0
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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