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

HRID 581234

反応式

HRID 581234 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1cda9e0edf02402882f40edfcf401c99
出典データセット
uspto-grants-1999_07
特許番号
US05919936

関連ノート

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