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

HRID 12886

반응식

HRID 12886 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-660058880d6144ccbdfae5625f97875b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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