2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride → N-[3-({2-[(N,N-dimethylglycyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 2391275

Reaktionsgleichung

Reaktionsgleichung von HRID 2391275
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16](=[O:21])[CH2:17][N:18]([CH3:20])[CH3:19])[N:14]=2)[N:11]=1.[CH3:25][N:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]([CH3:34])=[N:27]1>CN1CCCC1=O.[OH-].[Na+]>[CH3:19][N:18]([CH3:20])[CH2:17][C:16]([NH:15][C:13]1[N:14]=[C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:31]([C:30]4[N:26]([CH3:25])[N:27]=[C:28]([CH3:34])[CH:29]=4)=[O:32])[CH:24]=[CH:23][CH:22]=3)=[N:11][N:10]2[CH:12]=1)=[O:21]

Komponenten

5

Edukt 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 57708553N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-N2,N2-dimethylglycinamide

Produkt 1

HCID 24767980N-[3-({2-[(N,N-dimethylglycyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-N2,N2-dimethylglycinamide (196 mg, 0.6 mmol) in N-methylpyrrolidone (5.0 mL) was added 1,3-dimethylpyrazole-5-carbonyl chloride (270 mg, 1.7 mmol), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→460/40) and precipitated from ethyl acetate to give the title compound (131 mg, 49%) as a white powder. melting point 210° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→460/40)
  4. customprecipitated from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bb0344d669744857a7803d339af9601e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273741B2

Verknüpfte Notizen

Wird geladen…