Acetic Anhydride → 5-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine

HRID 398852

반응식

HRID 398852 반응식
[C:1]([NH:4][C:5]1[N:10]=[C:9]2[CH:11]=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[K+].[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C(OC(=O)C)(=O)C>CO>[C:1]([NH:4][C:5]1[N:10]=[C:9]2[C:11]([C:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH:19]=3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 196015015-(N-acetylamino)pyrrolo[3,2-b]pyridine

생성물 1

HCID 99035405-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine수율 59%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 0.477 gm (2.7 mMol) of the 5-(N-acetylamino)pyrrolo[3,2-b]pyridine, 0.54 mg (9.5 mMol) potassium hydroxide, and 0.43 mL (3.5 mMol) 1-methyl-4-piperidone in 15 mL methanol was heated at reflux for 18 hours. The reaction mixture was then concentrated under reduced pressure and the residue dissolved in pyridine. To this solution was added 0.20 mL (2.2 mMol) acetic anhydride and the resultant mixture stirred for 1 hour. This reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of ethyl acetate (2-40% methanol). Fractions containing product were combined and concentrated under reduced pressure to provide 0.43 gm (59%) 5-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine as an ivory foam. A portion was recrystallized from methanol/ethyl acetate to provide an analytical sample.

후처리

  1. temperatureat reflux for 18 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. dissolutionthe residue dissolved in pyridine
  4. concentrationThis reaction mixture was concentrated under reduced pressure
  5. washeluting with a gradient of ethyl acetate (2-40% methanol)
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-52a18e28688249298d3529890fa6ea21
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817671

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