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

HRID 1008348ノート

反応式

HRID 1008348 の反応式
[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][CH2:40][CH2:41][NH2:42].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:42][CH2:41][CH2:40][CH2:39][CH2:38][F:37])=[O:34])=[C:18]([F:23])[CH:17]=1

参加物

8

反応物 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 226671044-Fluorobutan-1-amine hydrochloride

生成物 1

HCID 69351783N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-(4-fluorobutyl)urea収率 58.3%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in toluene (6 ml) and triethylamine (1.0 ml) with heating, and a solution of triphosgene (104 mg) in dichloromethane (1.0 ml) was then added to the solution. The mixture was heated under reflux for 5 min. Next, 4-fluorobutylamine hydrochloride (55 mg) was added to the reaction solution, and the mixture was heated under reflux for additional 2 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with chloroform. The chloroform 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 80 mg (yield 55%) of the title compound.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 2 hr
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe chloroform 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)

出典と根拠

ORDレコード
ord-2181f2f8c7eb4a7db4345a872da07056
出典データセット
uspto-grants-2004_09
特許番号
US06797823B1

反応ノート

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