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

HRID 12886

反応式

HRID 12886 の反応式
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(O[CH:12]=[C:13]([C:19]#[N:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C.C([O-])(=O)C.[Na+]>C(O)C>[CH2:17]([O:16][C:14]([C:13]1[CH:12]=[N:8][N:7]([CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)[C:19]=1[NH2:20])=[O:15])[CH3:18]

参加物

5

反応物 3

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 212349Cyclopentylhydrazine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 12508126ethyl 5-amino-1-cyclopentyl-1H-pyrazole-4-carboxylate収率 79.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Cyclopentyl-hydrazine hydrochloride (1.000 g; 7.32 mmol), ethyl (ethoxymethylene)-cyanoacetate (1.026 g, 6.61 mmol) and anhydrous sodium acetate (0.644 g, 7.85 mmol) were combined in ethanol (10 mL) and heated at 70° C. for 20 hours. After cooling to room temperature, ethanol was removed in vacuo and the residue was partitioned between methylene chloride and water. The organic phase was washed sequentially with water and brine. Each aqueous phase was back extracted with a single portion of methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated. Purification by flash chromatography, eluting with 10-40% EtOAc/hexanes yielded 5-amino-1-cyclopentyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.170 g, 73%). Mass spectrum: m/z: 224.1 (M+H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customethanol was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. washThe organic phase was washed sequentially with water and brine
  5. extractionEach aqueous phase was back extracted with a single portion of methylene chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by flash chromatography
  9. washeluting with 10-40% EtOAc/hexanes

出典と根拠

ORDレコード
ord-660058880d6144ccbdfae5625f97875b
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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