Ethanamine, 2-fluoro-, hydrochloride → HCID 15515590, compound

HRID 1008346Notes

Reaction equation

HRID 1008346 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.Cl.[F:37][CH2:38][CH2:39][NH2:40].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.ClCCl.C(N(CC)CC)C>[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:40][CH2:39][CH2:38][F:37])=[O:34])=[C:18]([F:23])[CH:17]=1

Participants

8

Reactant 4

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 15515590HCID 15515590, compoundYield 145.6%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in toluene (10 ml) and triethylamine (0.5 ml) with heating. A solution of triphosgene (47 mg) in dichloromethane (1.0 ml) was then added to the solution, and the mixture was heated under reflux for 5 min. Next, 2-fluoroethylamine hydrochloride (42 mg) was added thereto, and the mixture was heated under reflux for additional 8 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. 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 93 mg (yield 72%) 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 8 hr
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1)

Sources & evidence

ORD record
ord-fe6648d877f945a386f72907a950798c
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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