Reaction #977432

Reaction equation

1,4-phenylene diisocyanate

6-amino-4-dimethylamino-2-methylquinoline

→

1-(4-dimethylamino-2-methylquinolin-6-yl)-3-{4-[3-(4-dimethylamino-2-methylquinolin-6-yl)ureido]phenyl}urea

Yield 48.3%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   OtherThe suspension obtained
2. 2
   Filtrationfiltered on sintered glass
3. 3
   Washthe solid residue is washed with 10 mL of a dichloromethane-methanol (90-10 by volume) mixture
4. 4
   OtherThe filtrate obtained
5. 5
   Concentrationis concentrated under air stream at a temperature in the region of 50° C

Procedure

A solution of 25 mg of 1,4-phenylene diisocyanate and 62.8 mg of 6-amino-4-dimethylamino-2-methylquinoline in 1 mL of dimethylformamide is stirred at a temperature in the region of 20° C. for 5 hours. 2 mL of dimethylformamide, 218 mg of polystyrene-isocyanate resin (Argonaut, 1.49 mmol/g) and 42 mg of polystyrene-trisamine resin (Argonaut, 3.75 mmol/g) are then added to the reaction mixture. The suspension obtained is stirred at a temperature in the region of 20° C. for 17 hours, filtered on sintered glass, and then the solid residue is washed with 10 mL of a dichloromethane-methanol (90-10 by volume) mixture. The filtrate obtained is concentrated under air stream at a temperature in the region of 50° C. 42.4 mg of 1-(4-dimethylamino-2-methylquinolin-6-yl)-3-{4-[3-(4-dimethylamino-2-methylquinolin-6-yl)ureido]phenyl}urea are thus obtained in the form of a yellow solid.

Source