Cyclopentylhydrazine hydrochloride → Cyclopentyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 12891

반응식

HRID 12891 반응식
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:9]([O:11][C:12](=[O:24])[C:13](=[CH:20]N(C)C)[C:14](=O)[C:15]([F:18])([F:17])[F:16])[CH3:10].C([O-])(=O)C.[Na+]>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[CH:20]=[N:8][N:7]([CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)[C:14]=1[C:15]([F:16])([F:17])[F:18])=[O:24])[CH3:10]

참가 물질

5

반응물 3

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

생성물 1

HCID 63235074Cyclopentyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester수율 52.6%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

Cyclopentyl-hydrazine hydrochloride (0.250 g, 1.83 mmol, Example 64, Step 2), 2-dimethylaminomethylene-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester (0.403 g, 1.68 mmol) and anhydrous sodium acetate (0.163 g, 1.99 mmol) were combined in ethanol (2.5 mL) and heated at 70° C. for 17 hours. After cooling to room temperature, the reaction mixture was partitioned between methylene chloride and water. The organic phase was washed with water and brine. Each aqueous phase was back extracted with a second portion of methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography, eluting with a 10-40% ethyl acetate-hexanes gradient, yielded 1-cyclopentyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.244 g, 52%). Mass spectrum: m/z: 277.1 (M+H).

후처리

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

출처 및 근거

ORD 기록
ord-c4b6d49295c04785a4247f88d64849e0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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