Add: A mixture of 5-chloro-8-hydroxyquinoline-7-carboxylic acid ( 0.50 g , 2.24 mmol ) , benzylamine ( 0.29 g , 2.68 mmol ) , 1-hydroxy-7-azabenzotriazole ( 0.36 g , 2.68 mmol ) , 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride ( 0.51 g , 2.68 mmol ) , and triethylamine ( 0.62 mL , 4.47 mmol ) in DMF ( 15 mL ) 
Dissolve: triethylamine ( 0.62 mL , 4.47 mmol ) in DMF ( 15 mL ) 
Stir: was stirred at room temperature overnight 
Concentrate: The reaction mixture was concentrated under vacuum 
Dissolve: The residue was dissolved in DMSO 
Degass: subjected to HPLC purification on C-18 stationary phase 
Wash: eluted with water / acetonitrile / TFA mobile phase 
Yield: Collection and lyophilization of appropriate fractions provide the title compound as yellow solid 
