2-Pyridinemethanamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-(2-pyridylmethyl)urea

HRID 1375784Notes

Reaction equation

HRID 1375784 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[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C.ClCCl.C(Cl)(Cl)Cl>[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[CH:22]=[CH:21][C:19]([NH:20][C:28]([NH:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[O:34])=[C:18]([F:23])[CH:17]=1

Participants

9

Reactant 4

HCID 195092-PyridinemethanamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 15515591N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-(2-pyridylmethyl)ureaYield 88%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in toluene (5 ml) and triethylamine (1 ml). A solution of triphosgene (104 mg) in dichloromethane was then added to the solution, and the mixture was refluxed for 5 min. Next, 2-(aminomethyl)pyridine (40 μl) was added thereto, and the mixture was heated under reflux for 2 hr. A saturated aqueous sodium hydrogencarbonate solution (1 ml) and chloroform (2 ml) were added to the reaction solution. The mixture was supported on diatomaceous earth, followed by extraction with chloroform. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol (8/1) to give 126 mg (yield 88%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 5 min
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hr
  4. extractionfollowed by extraction with chloroform
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol (8/1)

Sources & evidence

ORD record
ord-6b6c3162195748898444f64d59c87998
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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