N,N-二甲基甲酰胺 → N-(4-{[6-Methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl)-N'-(2-methoxyphenyl)urea

HRID 1375813笔记

反应方程式

HRID 1375813 反应方程式
[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][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[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-]>[CH3:41][O:40][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[O:8][CH2:1][CH2:2][O:47][CH3:46])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])=[O:28])=[C:22]([CH3:38])[C:21]=1[CH3:39]

参与物

6

反应物 3

HCID 6228N,N-二甲基甲酰胺HCID 22667072N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylphenyl)-N'-(2-methoxyphenyl)-ureaHCID 178418361HCID 178418361，化合物

产物 1

HCID 22667149N-(4-{[6-Methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl)-N'-(2-methoxyphenyl)urea

试剂、催化剂与溶剂 2

HCID 9942167氢氧化钯催化剂HCID 8471三乙胺溶剂

反应条件

温度
70 °C

实验过程

N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylphenyl)-N′-(2-methoxyphenyl)urea (161 mg) was dissolved in N,N-dimethylformamide (4 ml) and triethylamine (1 ml), and palladium hydroxide (32 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 washed with chloroform/methanol. The solvent was removed by distillation under the reduced pressure. A 110 mg portion of the residue (223 mg) was dissolved in N,N-dimethylformamide (1.5 ml), and potassium carbonate (23 mg), tetra-n-butylammonium iodide (5 mg), and 2-bromoethyl methyl ether (23 mg) were added to the solution. The mixture was stirred at 70° C. overnight. A saturated aqueous sodium hydroqencarbonate 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 89 mg of the title compound.

后处理

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas washed with chloroform/methanol
  3. customThe solvent was removed by distillation under the reduced pressure
  4. dissolutionA 110 mg portion of the residue (223 mg) was dissolved in N,N-dimethylformamide (1.5 ml)
  5. additionpotassium carbonate (23 mg), tetra-n-butylammonium iodide (5 mg), and 2-bromoethyl methyl ether (23 mg) were added to the solution
  6. additionA saturated aqueous sodium hydroqencarbonate 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)

来源与证据

ORD记录
ord-02183a03a8b0493fa1962a96a3486cdc
来源数据集
uspto-grants-2007_01
专利号
US07169789B2

反应笔记

加载中…