Potassium Carbonate → 6-bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine

HRID 2357605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357605
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH2:24])[CH3:20]>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:24][CH2:23][CH2:22][N:21]([CH2:25][CH3:26])[CH2:19][CH3:20])=[N:7][N:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 60993N,N-DiethylethylenediamineHCID 220304246-Bromo-1-chlorophthalazine

Produkt 1

HCID 684546736-bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6-Bromo-1-chlorophthalazine (0.22 g, 0.91 mmol) was dissolved in N,N-dimethylformamide (3 mL) and potassium carbonate (0.25 g, 1.81 mmol) and N1,N1-diethylethane-1,2-diamine (0.25 mL, 1.81 mmol) were added. The reaction mixture was heated to 80° C. for 5 h, cooled to ambient temperature and stirred for 16 h. The reaction mixture was diluted with 20 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous) and once with aqueous brine, separated, dried over sodium sulfate, and concentrated via rotovap to give crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 323(M+H)+.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. additionadded to an addition funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washThe organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous)
  5. customonce with aqueous brine, separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap
  8. customto give crude product
  9. customThe crude was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-716d62a92dbf4913a5d22346c3782f3a
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759337B2

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