海萝胶 → 3-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil

HRID 366314

反应方程式

HRID 366314 反应方程式
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.C1CCN2C(=NCCC2)CC1.[Cl:24][C:25]1[C:30]2[CH:31]=[C:32]([CH2:34][CH3:35])[O:33][C:29]=2[C:28]([NH:36][C:37](OC2C=CC=CC=2)=[O:38])=[C:27]([F:46])[CH:26]=1.Cl>CN(C)C=O>[Cl:24][C:25]1[C:30]2[CH:31]=[C:32]([CH2:34][CH3:35])[O:33][C:29]=2[C:28]([N:36]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:37]2=[O:38])=[C:27]([F:46])[CH:26]=1

参与物

6

反应物 4

HCID 313海萝胶HCID 81184DBUHCID 57025293-氨基-4,4,4-三氟巴豆酸乙酯HCID 232891804-Chloro-2-ethyl-6-fluoro-7-phenoxycarbonylaminobenzofuran

产物 1

HCID 232891763-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil收率 44%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
60 °C

实验过程

80 ml of N,N-dimethylformamide was added to 5.8 g (32 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate and 6.6 g (43 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene, and 9.6 g (29 mmol) of 4-chloro-2-ethyl-6-fluoro-7-phenoxycarbonylaminobenzofuran was gradually added thereto at room temperature. After stirring at 60° C. for 8 hours, the reaction solution was poured into a 10% hydrochloric acid aqueous solution and acidified, and then extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 4.8 g (yield: 44%) of the desired product as white crystals. Melting point: 154-155° C.

后处理

  1. additionwas gradually added
  2. customat room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water
  5. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

来源与证据

ORD记录
ord-8111caab964842e98b7fbc19b9ef2c26
来源数据集
uspto-grants-2000_10
专利号
US06130187

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