Allylamine → HCID 69353451, compound

HRID 1375785Notes

Reaction equation

HRID 1375785 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.[CH2:36]([NH2:39])[CH:37]=[CH2:38].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C.ClCCl.C(Cl)(Cl)Cl>[CH2:36]([NH:39][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])[CH:37]=[CH2:38]

Participants

9

Reactant 4

HCID 7853AllylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 69353451HCID 69353451, compoundYield 98.9%

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), 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, allylamine (22 mg) was added to the reaction solution, and the mixture was heated under reflux for additional 4 hr. A saturated aqueous sodium hydrogencarbonate solution (1 ml) and chloroform (2 ml) were added to the reaction solution, and 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/acetone (2/1) to give 125 mg (yield 98%) 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 additional 4 hr
  5. extractionfollowed by extraction with chloroform
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1)

Sources & evidence

ORD record
ord-377a42c512014817ae08822d7c33e4a5
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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