2,4-Dioxo-4-phenyl-butyric acid ethyl ester → 1-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester

HRID 1437259ノート

反応式

HRID 1437259 の反応式
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=1)[NH2:2].[CH2:11]([O:13][C:14](=[O:26])[C:15](=O)[CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:1]([C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=2)[N:2]=1)=[O:26])[CH3:12]

参加物

4

反応物 2

HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl esterHCID 230902452-Hydrazinyl-5-methoxypyridine

生成物 1

HCID 684408421-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The above-obtained 2-hydrazino-5-methoxypyridine (705 mg) and the 2,4-dioxo-4-phenylbutyric acid ethyl ester (1.12 g) prepared in Referential Example 123-1) in ethanol (25 mL) was refluxed under heat for 19 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, and the residue was partitioned by use of ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel chromatography (hexane-ethyl acetate), to thereby give 1-(5-methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester as an amorphous product (705 mg, 43%).

後処理

  1. temperaturewas refluxed
  2. temperatureunder heat for 19 hours
  3. temperaturecooled in air
  4. customThe reaction solvent was removed under reduced pressure
  5. customthe residue was partitioned by use of ethyl acetate and saturated aqueous sodium hydrogencarbonate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate anhydrate
  8. filtrationfollowed by filtration
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified through silica gel chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-a2b5440d4ba44d7499dee296ea7d76ee
出典データセット
uspto-grants-2009_11
特許番号
US07622471B2

反応ノート

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