Reaktion #1755222

Reaktionsgleichung

N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

1-methyl-1H-imidazole-2-carboxylic acid

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

1-hydroxybenzotriazole

sodium hydrogencarbonate

→

title compound

Ausbeute 12.0%

N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1-methyl-1H-imidazole-2-carboxamide

Ausbeute 12.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate/tetrahydrofuran
2. 2
   Waschenwashed with saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Filtrationfiltrated
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe obtained residue was purified by silica gel column chromatography (ethyl acetate alone)

Vorschrift

To a solution of N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.61 mmol) in N,N-dimethylformamide (4.0 mL) were added 1-methyl-1H-imidazole-2-carboxylic acid (154 mg, 1.22 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (351 mg, 1.83 mmol) and 1-hydroxybenzotriazole (248 mg, 1.83 mmol), and the mixture was stirred at room temperature for 16 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate alone) to give the title compound (31 mg, 12%) as a white powder.

Quelle