Sec-Butylamine → N-(sec-Butyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}urea

HRID 1008352Notes

Reaction equation

HRID 1008352 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.[CH:36]([NH2:40])([CH2:38][CH3:39])[CH3:37]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[CH:36]([NH:40][C:28]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:17][C:18]=1[F:23])=[O:34])([CH2:38][CH3:39])[CH3:37]

Participants

7

Reactant 3

HCID 24874Sec-ButylamineHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 22667117N-(sec-Butyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}ureaYield 89%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in chloroform (5 ml) and triethylamine (1 ml), and a solution of triphosgene (104 mg) in dichloromethane was then added to the solution. The mixture was heated under reflux for 5 min. Next, sec-butylamine (48 μl) was added to the reaction solution. The mixture was heated under reflux for 10 min. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (8/2) to give 117 mg (yield 89%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 10 min
  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/acetone (8/2)

Sources & evidence

ORD record
ord-531e6bd57bb74ea5ba2964f36753e941
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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