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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 1914177
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1914177
[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
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Komponenten

10

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1fddf4a15aeb46e0a6080db9d768ed68
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08609848B2

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