Reaktion #474931

Reaktionsgleichung

Cyclopropylamine

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

1-hydroxy-1H-benzotriazole

N-(4-(6-Cyano-7-(3-carboxypropoxy)-4-quinolyl)oxy-2-fluorophenyl)-N′-(4-fluorophenyl)urea

sodium hydroxide water

→

title compound

N-(4-(6-Cyano-7-(3-((cyclopropylamino)carbonyl)propoxy)-4-quinolyl)oxy-2-fluorophenyl)-N′-(4-fluorophenyl)urea

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 18 hours
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Waschenthe obtained organic layer was washed with saturated saline
6. 6
   Trocknendried over magnesium sulfate
7. 7
   EinengenThe organic layer was concentrated
8. 8
   Waschenthe obtained solid was washed with ether

Vorschrift

N-(4-(6-Cyano-7-(3-carboxypropoxy)-4-quinolyl)oxy-2-fluorophenyl)-N′-(4-fluorophenyl)urea (100 mg) was dissolved in dimethylformamide (3 ml), and then 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (44 mg) and 1-hydroxy-1H-benzotriazole (35 mg) were added while stirring on ice and the mixture was stirred at room temperature for 30 minutes. Cyclopropylamine (16 μl) was then added and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction solution was poured into 1N sodium hydroxide water and extracted with ethyl acetate, and the obtained organic layer was washed with saturated saline and dried over magnesium sulfate. The organic layer was concentrated, and the obtained solid was washed with ether and a small amount of ethyl acetate to obtain 38 mg of the title compound.

Quelle