HCID 10222330, compound → 2-(4-Ethoxyphenyl)-3-[4-(methylsulfonyl)phenyl]pyrazolo[1,5-b]pyridazine

HRID 392858Notes

Reaction equation

HRID 392858 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:17]3[N:12]([N:13]=[CH:14][CH:15]=[CH:16]3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]>C(Cl)Cl.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[C:17]3[N:12]([N:13]=[CH:14][CH:15]=[CH:16]3)[N:11]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 10222330HCID 10222330, compound

Product 1

HCID 98326872-(4-Ethoxyphenyl)-3-[4-(methylsulfonyl)phenyl]pyrazolo[1,5-b]pyridazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

The residue from Example 6(i), 2-(4-ethoxyphenyl)-3-(4-methanesulfonyl-phenyl)-3,3a-dihydro-pyrazolo[1,5-b]pyridazine, was redissolved in DCM (5 mL) and palladium on carbon (10% wt, 0.25 g) was added. The mixture was heated under reflux for 18 hours, whereupon analysis of the mixture by mass spectrometry showed the presence of a main component, MH+ 394, corresponding to the title compound. The reaction mixture was purified directly by silica gel chromatography (ethyl acetatelcyclohexane 2:1) to give the title compound as a white solid (0.181 g, 59%). MH+ 394

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours, whereupon analysis of the mixture by mass spectrometry

Sources & evidence

ORD record
ord-89f0b709318441f387cc386bbaf073d4
Source dataset
uspto-grants-2004_10
Patent number
US06803463B2

Reaction notes

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