Diethyl Ether → 4-(6,7-Dimethoxy-4-quinazolinyl)-N-(3-pyridyl)-1-piperazinecarboxamide

HRID 1533133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533133
Cl.C(Cl)(=O)[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[N-:11]=[N+]=[N-].[Na+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]=[CH:22][N:21]=[C:20]2[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C([O:37][CH2:38]C)C>>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]=[CH:22][N:21]=[C:20]2[N:29]1[CH2:30][CH2:31][N:32]([C:38]([NH:11][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[O:37])[CH2:33][CH2:34]1

Komponenten

5

Edukt 4

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 27584846,7-Dimethoxy-4-piperazin-1-yl-quinazoline

Produkt 1

HCID 111120144-(6,7-Dimethoxy-4-quinazolinyl)-N-(3-pyridyl)-1-piperazinecarboxamideAusbeute 25 %

Versuchsvorschrift

To a suspension of 5.9 g (33 mmol) of nicotinoyl chloride hydrochloride in 50 ml of diethyl ether was added 50 ml of an aqueous solution of 12.0 g (185 mmol) of sodium azide under ice-cooling, followed by vigorous stirring at room temperature. After the organic layer was separated, the water layer was extracted with ether. Then, the combined organic layers were washed with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. After the solvent was evaporated at a temperature below 30° C., the residue was dissolved in 40 ml of toluene. To the resulting solution was added 548 mg (2.00 mmol) of 6,7-dimethoxy-4-piperazinylquinazoline obtained according to the method described in South African Patent No.67 06512 (1968), followed by heating at 70° C. with stirring for 3 hours. After the reaction mixture was allowed to cool to room temperature, the solvent was evaporated, and the residue was purified by silica gel chromatography and recrystallized from ethyl acetate to give the desired compound as colorless crystals.

Aufarbeitung

  1. temperaturecooling
  2. customAfter the organic layer was separated
  3. extractionthe water layer was extracted with ether
  4. washThen, the combined organic layers were washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customAfter the solvent was evaporated at a temperature below 30° C.
  7. dissolutionthe residue was dissolved in 40 ml of toluene
  8. customobtained
  9. temperatureby heating at 70° C.
  10. stirringwith stirring for 3 hours
  11. temperatureto cool to room temperature
  12. customthe solvent was evaporated
  13. customthe residue was purified by silica gel chromatography
  14. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7f16b44840a24906b560a60a9b5d7cb7
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207667B1

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