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Carbon Dioxide → 2-(1-{[5-(Difluoromethoxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524249
Notes
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Reaction equation

HRID 524249 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12]([CH3:34])([CH3:33])[C:13](=[O:32])[N:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([C:24]4[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][C:25]=4[CH3:31])=[O:23])[CH2:18][CH2:17]3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)=O.C1COCC1.Cl[CH:44]([F:46])[F:45]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.O1CCOCC1.O.C(OCC)C>[F:45][CH:44]([F:46])[O:30][C:28]1[CH:27]=[CH:26][C:25]([CH3:31])=[C:24]([C:22]([N:19]2[CH2:20][CH2:21][CH:16]([N:14]3[C:13](=[O:32])[C:12]([CH3:34])([CH3:33])[C:11]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:15]3)[CH2:17][CH2:18]2)=[O:23])[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 280Carbon DioxideHCID 6372ChlorodifluoromethaneHCID 8028TetrahydrofuranHCID 462020675-(3,4-Dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 673654622-(1-{[5-(Difluoromethoxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 5

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

In a pressure vessel 0.47 g of 5-(3,4-dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 85) and 37 mg tetrabutylammonium iodide are solved in a mixture of 20 ml methanol and 5 ml dioxane. After the reaction mixture has been frozen to a solid block upon cooling with dry ice, a layer of 4 ml THF is placed above the frozen reaction mixture and the pressure vessel is charged with 2.8 g of chloro(difluoro)methane. The pressure vessel is heated for 90 minutes to 70° C. and after the reaction mixture has reached RT, it is portioned between diethyl ether and water. After separation of the phases, the organic phase is washed with brine, dried over MgSO4, and the solvents are removed under reduced pressure. The crude product is purified by chromatography (silica gel and DCM) to yield the title compound.

Workup

  1. temperatureAfter the reaction mixture has been frozen to a solid block
  2. temperatureThe pressure vessel is heated for 90 minutes to 70° C.
  3. customhas reached RT
  4. customAfter separation of the phases
  5. washthe organic phase is washed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvents are removed under reduced pressure
  8. customThe crude product is purified by chromatography (silica gel and DCM)

Sources & evidence

ORD record
ord-2ef01a8f0b054693a90f7b3f28abd1c2
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09340522B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes