Olprinone → 2-Chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methylpyridine-3-carbonitrile

HRID 414318

反応式

HRID 414318 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([C:18]#[N:19])[C:13](=O)[NH:14][C:15]=3[CH3:16])[CH:7]=[CH:6][C:5]=12.P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[Cl:22][C:13]1[C:12]([C:18]#[N:19])=[CH:11][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=2)=[C:15]([CH3:16])[N:14]=1

参加物

4

反応物 2

HCID 4593OlprinoneHCID 24813Phosphorus oxychloride

生成物 1

HCID 138523142-Chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methylpyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

実験手順

A mixture of 3.1 g of 1,2-dihydro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methyl-2-oxo-3-pyridinecarbonitrile, 30 ml of phosphorous oxychloride and 5 drops of dimethylformamide was stirred under reflux for 2 hours. An excess of phosphorous oxychloride was removed by distillation under reduced pressure and upon cooling, chloroform, a 20% NaOH solution and then an aqueous sodium carbonate solution were added to the residue to render it alkaline. The organic layer was taken by fractionation. After the chloroform layer was dried over magnesium sulfate, chloroform was removed by distillation. The residue was purified by column chromatography to obtain 1.9 g of 2-chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methyl-3-pyridinecarbonitrile.

後処理

  1. temperatureunder reflux for 2 hours
  2. customAn excess of phosphorous oxychloride was removed by distillation under reduced pressure
  3. temperatureupon cooling
  4. additionchloroform, a 20% NaOH solution and then an aqueous sodium carbonate solution were added to the residue
  5. dry with materialAfter the chloroform layer was dried over magnesium sulfate, chloroform
  6. customwas removed by distillation
  7. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-3ee0a0e1d33743088a9f222cf85b48e9
出典データセット
uspto-grants-1988_12
特許番号
US04791202

関連ノート

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