Cyanoacetamide → Olprinone

HRID 414313

Reaktionsgleichung

Reaktionsgleichung von HRID 414313
CN(C)[CH:3]=[C:4]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[CH:13]=1)[C:5](=O)[CH3:6].[C:18]([CH2:20][C:21]([NH2:23])=[O:22])#[N:19].C[O-].[Na+]>CN(C)C=O>[CH3:6][C:5]1[NH:23][C:21](=[O:22])[C:20]([C:18]#[N:19])=[CH:3][C:4]=1[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[CH:13]=1

Komponenten

5

Edukt 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 541278533-Buten-2-one, 4-(dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-

Produkt 1

HCID 4593OlprinoneAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 230 ml of N,N-dimethylformamide was dissolved 23.5 g of 4-dimethylamino-3-(imidazo[1,2-a]pyridin-6-yl)-3-buten-2-one. The solution was stirred at 80° to 90° C. for 12 hours, together with 9.48 g of α-cyanoacetamide and 12.2 g of sodium methoxide. After cooling, the solvent was removed by distillation under reduced pressure and 500 ml of water was added to the residue to dissolve it. The solution was washed with 600 ml of chloroform. Next, about 5 ml of acetic acid was added to the aqueous layer to adjust pH to 6.5. Crystals precipitated upon cooling were taken by filtration. After the crystals were washed with water, acetonitrile and then ether, they were dissolved in 200 ml of a 2.5% aqueous sodium hydroxide solution. The solution was treated with activated charcoal. The filtrate was again adjusted to pH of 6.5 with about 7 ml of acetic acid. Crystals precipitated upon cooling were taken by filtration. After the crystals were washed with water, acetonitrile and then ether, they were recrystallized from 100 ml of N,N-dimethylformamide to obtain 13 g of 1,2-dihydro-6-methyl-2-oxo-5-(imidazo[1,2-a]pyridin-6-yl)-3-pyridinecarbonitrile.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was removed by distillation under reduced pressure and 500 ml of water
  3. additionwas added to the residue
  4. dissolutionto dissolve it
  5. washThe solution was washed with 600 ml of chloroform
  6. additionNext, about 5 ml of acetic acid was added to the aqueous layer
  7. customCrystals precipitated
  8. temperatureupon cooling
  9. filtrationwere taken by filtration
  10. washAfter the crystals were washed with water, acetonitrile
  11. dissolutionether, they were dissolved in 200 ml of a 2.5% aqueous sodium hydroxide solution
  12. additionThe solution was treated with activated charcoal
  13. customCrystals precipitated
  14. temperatureupon cooling
  15. filtrationwere taken by filtration
  16. washAfter the crystals were washed with water, acetonitrile
  17. customether, they were recrystallized from 100 ml of N,N-dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-e96484f0ceef4348b973729183078f3c
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791202

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