Dimethylformamide → N-(2,4-Difluorophenyl)-N'-(4-{[6-methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl) urea

HRID 1008384ノート

反応式

HRID 1008384 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=4[F:37])=[O:28])=[C:22]([CH3:38])[C:21]=3[CH3:39])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:40][CH3:41])[C:2]1C=CC=CC=1.[H][H].CN(C)[CH:46]=[O:47]>C(N(CC)CC)C.[OH-].[Pd+2].[OH-]>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[NH:29][C:27]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([O:8][CH2:1][CH2:2][O:47][CH3:46])=[C:10]([O:40][CH3:41])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)=[C:21]([CH3:39])[C:22]=1[CH3:38])=[O:28]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 22667195N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl)oxy}-2,3-dimethylphenyl)-N'-(2,4-difluorophenyl)ureaHCID 178418361HCID 178418361、化合物

生成物 1

HCID 17819598N-(2,4-Difluorophenyl)-N'-(4-{[6-methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl) urea

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylphenyl)-N′-(2,4-difluorophenyl)urea (213 mg) was dissolved in N,N-dimethylformamide (5 ml) and triethylamine (1 ml), and palladium hydroxide (40 mg) was added to the solution. The mixture was stirred in a hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through Celite and was then washed with chloroform/methanol. The solvent was removed by distillation under the reduced pressure. A 90 mg portion of the residue (184 mg) was dissolved in N,N-dimethylformamide (1.5 ml), and potassium carbonate (32 mg), tetra-n-butylammonium iodide (7 mg), and 2-bromoethyl methyl ether (32 mg) were added to the solution. The mixture was stirred at 70° C. 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 anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with chloroform/acetone (2/1) to give 110 mg of the title compound.

後処理

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas then washed with chloroform/methanol
  3. customThe solvent was removed by distillation under the reduced pressure
  4. dissolutionA 90 mg portion of the residue (184 mg) was dissolved in N,N-dimethylformamide (1.5 ml)
  5. additionpotassium carbonate (32 mg), tetra-n-butylammonium iodide (7 mg), and 2-bromoethyl methyl ether (32 mg) were added to the solution
  6. additionA saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/acetone (2/1)

出典と根拠

ORDレコード
ord-5985467dab2c430f9a705b28b9cbb758
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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