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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
ノート
印刷プレビュー

反応式

HRID 1914177 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 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

生成物 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

試薬・触媒・溶媒 5

HCID 67553Tetrabutylammonium Iodide触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1fddf4a15aeb46e0a6080db9d768ed68
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08609848B2

反応ノート

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