Acetonitrile → 5,11-Dihydro-11-{2-[N-(4-methoxyphenethyl)-N-methylamino]acetyl}-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 36855

Reaktionsgleichung

Reaktionsgleichung von HRID 36855
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[N:20][C:6]1=2)=[O:4].[CH3:21][O:22][C:23]1[CH:32]=[CH:31][C:26]([CH2:27][CH2:28]CN)=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+].[C:38](#[N:40])C>>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH2:28][N:40]([CH2:2][C:3]([N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[NH:8][C:7]3[CH:17]=[CH:18][CH:19]=[N:20][C:6]2=3)=[O:4])[CH3:38])=[CH:31][CH:32]=1

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 516892Sodium BicarbonateHCID 30298153-(4-Methoxyphenyl)propan-1-amine

Produkt 1

HCID 99317235,11-Dihydro-11-{2-[N-(4-methoxyphenethyl)-N-methylamino]acetyl}-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Versuchsvorschrift

A mixture of 11-chloroacetyl-5,11-dihydro-6H-pyrido- [2,3-b][1,4]benzodiazepine-6-one (288 mg) (German patent 1,936,670), N-(4-methoxyphenethyl)methylamine (182 mg) and sodium hydrogen carbonate (92 mg) in acetonitrile (25 ml) was heated under reflux for 16 hours and evaporated. The residue was partitioned between 2M aqueous sodium hydrogen carbonate solution and dichloromethane and the organic layer washed with brine, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-10% methanol as eluant. Appropriate fractions were combined and evaporated and the residue crystallised from ethyl acetate to give the title compound as a colourless solid, 216 mg (52%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated
  4. customThe residue was partitioned between 2M aqueous sodium hydrogen carbonate solution and dichloromethane
  5. washthe organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica
  9. customevaporated
  10. customthe residue crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-80d480d22c604362833a5a9a03047339
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418229

Verknüpfte Notizen

Wird geladen…