聚(苯乙烯-二乙烯苯) → 6-Amino-4-benzylamino-2-furan-2-yl-nicotinonitrile

HRID 1356022

反应方程式

HRID 1356022 反应方程式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOC>[NH2:1][C:2]1[CH:3]=[C:4]([NH:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

参与物

4

反应物 2

HCID 7504聚(苯乙烯-二乙烯苯)HCID 86583754Trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester

产物 1

HCID 185073096-Amino-4-benzylamino-2-furan-2-yl-nicotinonitrile收率 38%

试剂、催化剂与溶剂 1

HCID 8071乙二醇二甲醚溶剂

反应条件

温度
80 °C

实验过程

To a stirred solution of 250 mg (0.75 mmol) trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester in 10 ml DME was added 0.82 ml (7.56 mmol) benzylamine and the mixture heated at 80° C. for 72 hours. The reaction mixture was then cooled to room temperature and partitioned between dichloromethane and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether/hexane to afford 79 mg (38%) 6-amino-4-benzylamino-2-furan-2-yl-nicotinonitrile as a white crystalline solid. ES-MS m/e (%): 291 (M+H+, 100).

后处理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between dichloromethane and water
  3. customThe phases were separated
  4. dry with materialthe organic phase dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in ether/hexane

来源与证据

ORD记录
ord-43d2dd40bb0f4550a44a7c264d7c75bc
来源数据集
uspto-grants-2003_07
专利号
US06586441B2

关联笔记

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