Chloroacetaldehyde → 7-(4-Bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acid

HRID 558228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558228
C([O:5][C:6]([C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[F:22])=[CH:12][C:11]([NH2:24])(Cl)[NH:10][N:9]=1)=[O:7])(C)(C)C.Cl[CH2:26][CH:27]=O>C(O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]2[C:8]([C:6]([OH:5])=[O:7])=[N:9][N:10]3[CH:26]=[CH:27][N:24]=[C:11]3[CH:12]=2)=[C:16]([F:22])[CH:17]=1

Komponenten

4

Edukt 2

HCID 33ChloroacetaldehydeHCID 66998716HCID 66998716, Verbindung

Produkt 1

HCID 595193857-(4-Bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspended solution of 6-amino-4-(4-bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester (61 mg, 0.16 mmol) in ethanol (5 ml) in a bomb reactor is added at room temperature chloroacetaldehyde (0.12 ml of 50% aqueous solution, 5.0 equivalents). The reaction mixture is sealed and stirred at 80° C. for two days, and then cooled to room temperature. The solvent is removed, and the residue is diluted with ethyl acetate (20 ml). The organic layer is washed with saturated NaCl (20 ml×3), dried over Na2SO4, and concentrated. The residue is purified by flash column chromatography to provide the desired product.

Aufarbeitung

  1. customThe reaction mixture is sealed
  2. temperaturecooled to room temperature
  3. customThe solvent is removed
  4. additionthe residue is diluted with ethyl acetate (20 ml)
  5. washThe organic layer is washed with saturated NaCl (20 ml×3)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f92e18c4da445d09abeec5c5929d182
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063049B2

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