Allyl chloroformate → 5-(N-[prop-1-en-3-yloxycarbonyl]amino)-3-(1-tert-butoxycarbonylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

HRID 581365노트

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HRID 581365 반응식
[NH2:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.Cl[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26]>N1C=CC=CC=1>[CH2:30]=[CH:29][CH2:28][O:27][C:25]([NH:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1)=[O:26]

참가 물질

4

반응물 2

HCID 18052Allyl chloroformate2회HCID 117268345-Amino-3-(1-tert-butoxycarbonylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

생성물 1

HCID 196015485-(N-[prop-1-en-3-yloxycarbonyl]amino)-3-(1-tert-butoxycarbonylpiperidin-4-yl)pyrrolo[3,2-b]pyridine수율 60%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
50 °C

실험 절차

A mixture of 4.0 gm (12.6 mMol) 5-amino-3-(1-tert-butoxycarbonylpiperidin-4-yl)pyrrolo[3,2-b]pyridine and 2.7 mL (25.2 mMol) allyl chloroformate in 200 mL pyridine was heated at 50° C. for 5 hours. At this point an additional 2 mL of allyl chloroformate were added and heating was continued for another 1.5 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue partitioned between 1N sodium hydroxide and chloroform. The phases were separated and the aqueous phase was extracted well with chloroform. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. This residue was dissolved in 2M ammonia in methanol for two hours. The reaction mixture was concentrated under reduced pressure and the residue subjected to flash silica gel chromatography, eluting with dichloromethane containing from 2-5% methanol and 1% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure. The residue was crystallized from aqueous ethanol to provide 2.9 gm (60%) 5-(N-[prop-1-en-3-yloxycarbonyl]amino)-3-(1-tert-butoxycarbonylpiperidin-4-yl)pyrrolo[3,2-b]pyridine.

후처리

  1. temperatureheating
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue partitioned between 1N sodium hydroxide and chloroform
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted well with chloroform
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThis residue was dissolved in 2M ammonia in methanol for two hours
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. washeluting with dichloromethane containing from 2-5% methanol and 1% ammonium hydroxide
  12. additionFractions containing product
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was crystallized from aqueous ethanol

출처 및 근거

ORD 기록
ord-41d1940f9caf4607a83ac3ffc9aaefde
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919936

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