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

HRID 890250Notes

Reaction equation

HRID 890250 reaction equation
[C:1]1([N:10]=[C:11]=[O:12])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([CH3:24])[CH:18]=[C:17]2[N:25]([CH3:27])[CH3:26]>CN(C)C=O>[CH3:27][N:25]([CH3:26])[C:17]1[C:16]2[C:21](=[CH:22][CH:23]=[C:14]([NH:13][C:8]([NH:7][C:4]3[CH:3]=[CH:2][C:1]([NH:10][C:11]([NH:13][C:14]4[CH:15]=[C:16]5[C:21](=[CH:22][CH:23]=4)[N:20]=[C:19]([CH3:24])[CH:18]=[C:17]5[N:25]([CH3:26])[CH3:27])=[O:12])=[CH:6][CH:5]=3)=[O:9])[CH:15]=2)[N:20]=[C:19]([CH3:24])[CH:18]=1

Participants

4

Reactant 2

HCID 610091,4-DiisocyanatobenzeneHCID 179088824-Dimethylamino-6-aminoquinaldine

Product 1

HCID 120524651-(4-Dimethylamino-2-methylquinolin-6-yl)-3-{4-[3-(4-dimethylamino-2-methylquinolin-6-yl)ureido]phenyl}ureaYield 48.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °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.

Workup

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

Sources & evidence

ORD record
ord-e61f52614bd343dab22c2e7bed72335e
Source dataset
uspto-grants-2006_02
Patent number
US06995175B2

Reaction notes

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