Olprinone → 5-(Imidazo[1,2-a]pyridin-6-yl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 579958Notes

Reaction equation

HRID 579958 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1.[OH2:20].N>S(=O)(=O)(O)O>[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]([NH2:10])=[O:20])=[CH:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 4593OlprinoneHCID 12896473Azane;hydrate

Product 1

HCID 138523295-(Imidazo[1,2-a]pyridin-6-yl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In 15 ml of conc. sulfuric acid, 3 g of 1,2-dihydro-6-methyl-5-(imidazo[1,2-a]pyridin-6-yl)-2-oxo-3-pyridinecarbonitrile was stirred at 90° C. for 40 minutes. After cooling, the reaction mixture was poured into ice and conc. ammonia water was added thereto to render alkaline. Crystals prepcipitated were taken by filtration. After washing with water and drying, the crystals were recrystallized from N,N-dimethylformamide to obtain 2.5 g of 1,2-dihydro-6-methyl-5-(imidazo[1,2-a]pyridin-6-yl)-2-oxo-3-pyridinecarboxamide.

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. filtrationCrystals prepcipitated were taken by filtration
  4. washAfter washing with water
  5. customdrying
  6. customthe crystals were recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-d57f150a31994a368fc586864fe0f06a
Source dataset
uspto-grants-1988_06
Patent number
US04751227

Reaction notes

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