2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → ethyl 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylate

HRID 12878

反応式

HRID 12878 の反応式
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(O[CH:13]=[C:14]([C:20]#[N:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C([O-])(=O)C.[Na+]>C(O)C>[CH2:18]([O:17][C:15]([C:14]1[CH:13]=[N:9][N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:20]=1[NH2:21])=[O:16])[CH3:19]

参加物

5

反応物 3

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 207836Cyclohexylhydrazine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 351028ethyl 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylate収率 92.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Cyclohexylhydrazine hydrochloride (3.057 g, 20.29 mmol, CAS #24214-73-1, purchased from Aldrich) was combined with ethyl (ethoxymethylene)-cyanoacetate (3.390 g, 20.04 mmol) and anhydrous sodium acetate (2.080 g, 25.36 mmol) in 30 mL ethanol. The mixture was heated at 70° C. for 16 hours then cooled to room temperature and concentrated. The residue was partitioned between methylene chloride and water. The separated aqueous phase was extracted with a second portion of methylene chloride. The organic phases were successively washed with water and brine and then combined, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography eluting with a gradient of 25-70% ethyl acetate/hexanes to give 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylic acid ethyl ester (4.42 g, 92%). Mass spectrum: m/z: 238.1 (M+H).

後処理

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between methylene chloride and water
  4. extractionThe separated aqueous phase was extracted with a second portion of methylene chloride
  5. washThe organic phases were successively washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. washeluting with a gradient of 25-70% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-5ca9e47eaaeb489c8850e026eadd480c
出典データセット
uspto-grants-2010_06
特許番号
US07728029B2

関連ノート

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