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

HRID 414328Notes

Reaction equation

HRID 414328 reaction equation
[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

Participants

4

Reactant 2

HCID 4593OlprinoneHCID 31398Chlorosuccinimide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0c3211dd772b47cf82fc406c26d00e28
Source dataset
uspto-grants-1988_12
Patent number
US04791203

Reaction notes

Loading…