Acetic Acid → N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-5-amine

HRID 2048571ノート

反応式

HRID 2048571 の反応式
C([N:8]1[C:12]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:16][CH2:15]2)=[CH:11][CH:10]=[N:9]1)C1C=CC=CC=1.C(O)(=O)C.C([O-])=O.[NH4+].C(OCC)(=O)C>C(O)C.[OH-].[Pd+2].[OH-]>[Si:21]([O:20][CH:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:12]2[NH:8][N:9]=[CH:10][CH:11]=2)[CH2:15][CH2:16]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 670086441-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-5-amine

生成物 1

HCID 67010200N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-5-amine収率 69%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 1-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-5-amine (1.3 g) and palladium hydroxide (10 wt %, 1.27 g) in ethanol (6 mL)-acetic acid (0.6 mL) was added ammonium formate (0.62 g) by small portions at 80° C. After stirring at 80° C. for 2 hr, the mixture was allowed to cool, ethyl acetate was added, and the insoluble material was filtered off. Saturated aqueous sodium hydrogen carbonate was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.68 g, 69%).

後処理

  1. temperatureto cool
  2. filtrationthe insoluble material was filtered off
  3. additionSaturated aqueous sodium hydrogen carbonate was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-eb7405fddb5f4fb7b4cb3db389e9d2ac
出典データセット
uspto-grants-2013_11
特許番号
US08592431B2

反応ノート

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