Triphosgene → N-(5-Bromo-6-methyl-2-pyridyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}urea

HRID 1375805

反応式

HRID 1375805 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[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[NH2:37][C:38]1[N:43]=[C:42]([CH3:44])[C:41]([Br:45])=[CH:40][CH:39]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Br:45][C:41]1[CH:40]=[CH:39][C:38]([NH:37][C:29]([NH:20][C:19]2[CH:21]=[C:22]([CH3:23])[C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][C:18]=2[CH3:24])=[O:35])=[N:43][C:42]=1[CH3:44]

参加物

8

反応物 4

HCID 94429TriphosgeneHCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 516892Sodium BicarbonateHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

生成物 1

HCID 69353472N-(5-Bromo-6-methyl-2-pyridyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}urea収率 48.3%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (92 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 6-amino-3-bromo-2-methylpyridine (69 mg) was added to the reaction solution, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in a minor amount of chloroform, and a larger amount of ether was added to the solution to precipitate a crystal which was then collected by filtration to give 80 mg (yield 48%) of the title compound.

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. dissolutionThe residue was dissolved in a minor amount of chloroform
  6. additiona larger amount of ether was added to the solution
  7. customto precipitate a crystal which
  8. filtrationwas then collected by filtration

出典と根拠

ORDレコード
ord-36de0271f9b744cc88eb5c31291d1188
出典データセット
uspto-grants-2007_01
特許番号
US07169789B2

関連ノート

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