Triphosgene → N-(5-Bromo-6-methyl-2-pyridyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}urea

HRID 1375805

Reaction equation

HRID 1375805 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[NH2:37][C:38]1[N:43]=[C:42]([CH3:44])[C:41]([Br:45])=[CH:40][CH:39]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Br:45][C:41]1[CH:40]=[CH:39][C:38]([NH:37][C:29]([NH:20][C:19]2[CH:21]=[C:22]([CH3:23])[C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][C:18]=2[CH3:24])=[O:35])=[N:43][C:42]=1[CH3:44]

Participants

8

Reactant 4

HCID 94429TriphosgeneHCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 516892Sodium BicarbonateHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

Product 1

HCID 69353472N-(5-Bromo-6-methyl-2-pyridyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}ureaYield 48.3%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (92 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 6-amino-3-bromo-2-methylpyridine (69 mg) was added to the reaction solution, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in a minor amount of chloroform, and a larger amount of ether was added to the solution to precipitate a crystal which was then collected by filtration to give 80 mg (yield 48%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. dissolutionThe residue was dissolved in a minor amount of chloroform
  6. additiona larger amount of ether was added to the solution
  7. customto precipitate a crystal which
  8. filtrationwas then collected by filtration

Sources & evidence

ORD record
ord-36de0271f9b744cc88eb5c31291d1188
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Linked notes

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