Potassium Carbonate → HCID 69960056, compound

HRID 1291298Notes

Reaction equation

HRID 1291298 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].[Cl: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][N:14]([CH2:27][C:26]3[CH:25]=[CH:24][C:23]([C:21](=[O:22])[C:20]4[CH:31]=[CH:32][C:17]([Cl:16])=[CH:18][CH:19]=4)=[CH:30][CH:29]=3)[C:8]=2[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178434370HCID 178434370, compound

Product 1

HCID 69960056HCID 69960056, 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-chlorobenzoyl)benzyl bromide (1.2 g) and potassium carbonate (525 mg), and the mixture was stirred at room temperature for 15 hours. This reaction mixture was extracted with ethyl acetate-THF 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 n-hexane-diethyl ether, and dried. White powder, 527 g.

Workup

  1. extractionThis reaction mixture was extracted with ethyl acetate-THF
  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 n-hexane-diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-c1b54efcf02a4837ae8720d74aca092b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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