Olprinone → 5-(3-Chloroimidazo[1,2-a]pyridin-6-yl)-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile

HRID 414317

반응식

HRID 414317 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:17])[NH:14][C:15]=3[CH3:16])[CH:7]=[CH:6][C:5]=12.[Cl:20]N1C(=O)CCC1=O>CN(C)C=O>[Cl:20][C:3]1[N:4]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([C:18]#[N:19])[C:13](=[O:17])[NH:14][C:15]=3[CH3:16])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

참가 물질

4

반응물 2

HCID 4593OlprinoneHCID 31398Chlorosuccinimide

생성물 1

HCID 138523335-(3-Chloroimidazo[1,2-a]pyridin-6-yl)-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile수율 29.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In 10 ml of N,N-dimethylformamide, 0.3 g of 1,2-dihydro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methyl-2-oxo-3-pyridinecarbonitrile was stirred together with 0.19 g of N-chlorosuccinimide at 60° to 80° C. for 2 hours. After cooling, the solvent was removed by distillation under reduced pressure and water was added to the residue to take the solid by filtration. The solid was recrystallized from large quantities of methanol to obtain 0.1 g of 5-(3-chloroimidazo[1,2-a]pyridin-6-yl)-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile.

후처리

  1. temperatureAfter cooling
  2. customthe solvent was removed by distillation under reduced pressure and water
  3. additionwas added to the residue
  4. filtrationby filtration
  5. customThe solid was recrystallized from large quantities of methanol

출처 및 근거

ORD 기록
ord-162713cdd3f54dcc827ec8044f58ffc3
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791202

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