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

HRID 414318

반응식

HRID 414318 반응식
[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

참가 물질

4

반응물 2

HCID 4593OlprinoneHCID 24813Phosphorus oxychloride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3ee0a0e1d33743088a9f222cf85b48e9
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791202

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