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

HRID 12878

반응식

HRID 12878 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5ca9e47eaaeb489c8850e026eadd480c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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