Cyclopropanecarbonyl chloride → N-(Pyrazin-2-YL)cyclopropanecarboxamide

HRID 133073

반응식

HRID 133073 반응식
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1>N1C=CC=CC=1.ClCCl>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[NH:1][C:11]([CH:8]1[CH2:10][CH2:9]1)=[O:12]

참가 물질

5

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 78747Aminopyrazine

생성물 1

HCID 4047267N-(Pyrazin-2-YL)cyclopropanecarboxamide

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 10 g (105 mmol) of 2-aminopyrazine in 100 mL of pyridine was added dropwise a solution of 10.99 g (9.56 mL, 105 mmol) of cyclopropanecarbonyl chloride in 100 mL of dichloromethane. The resultant yellow solution was stirred at ambient temperature for 2 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and a small amount of water and washed sequentially with 1 M aqueous cuprous sulfate solution and water. The water layer was extracted with three portions of ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, and concentrated. Purification by flash chromatography (silica gel, eluting sequentially with 50%, 80% and 100% ethyl acetate/hexane) gave the title compound.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washa small amount of water and washed sequentially with 1 M aqueous cuprous sulfate solution and water
  4. extractionThe water layer was extracted with three portions of ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel
  9. washeluting sequentially with 50%, 80% and 100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5b9846e3a40944a59e65c0cb56916691
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390809B2

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