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

HRID 1375784ノート

反応式

HRID 1375784 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.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C.ClCCl.C(Cl)(Cl)Cl>[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:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[O:34])=[C:18]([F:23])[CH:17]=1

参加物

9

反応物 4

HCID 195092-PyridinemethanamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

生成物 1

HCID 15515591N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-(2-pyridylmethyl)urea収率 88%

試薬・触媒・溶媒 4

HCID 1140Toluene溶媒HCID 6212Chloroform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 (5 ml) and triethylamine (1 ml). A solution of triphosgene (104 mg) in dichloromethane was then added to the solution, and the mixture was refluxed for 5 min. Next, 2-(aminomethyl)pyridine (40 μl) was added thereto, and the mixture was heated under reflux for 2 hr. A saturated aqueous sodium hydrogencarbonate solution (1 ml) and chloroform (2 ml) were added to the reaction solution. 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/methanol (8/1) to give 126 mg (yield 88%) of the title compound.

後処理

  1. temperaturethe mixture was refluxed for 5 min
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hr
  4. extractionfollowed by extraction with chloroform
  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/methanol (8/1)

出典と根拠

ORDレコード
ord-6b6c3162195748898444f64d59c87998
出典データセット
uspto-grants-2007_01
特許番号
US07169789B2

反応ノート

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