2-[4-(2-Morpholin-4-ylethyl)phenyl]guanidine;nitric acid | 1006585-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-(2-Morpholin-4-ylethyl)phenyl]guanidine;nitric acid
• CAS: 1006585-18-7
• 化学式: C₁₃H₂₀N₄O*HNO₃
• 分子量: 311.341
• InChiKey: IQRAWBVRPOBURY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl [1-[4-[2-cyano-3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-1-methylethyl]carbamate 、 2-[4-(2-Morpholin-4-ylethyl)phenyl]guanidine;nitric acid 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以75%的产率得到1,1-dimethylethyl[1-[4-[5-cyano-2-[[4-[2-(4-morpholinyl)ethyl]phenyl]-amino]-4-pyrimidinyl]phenyl]-1-methylethyl]carbamate
  参考文献：
  名称：

  Scalable Synthesis of the VEGF-R2 Kinase Inhibitor JNJ-17029259 Using Ultrasound-Mediated Addition of MeLi−CeCl₃ to a Nitrile

  摘要：

  [GRAPHICS]The preparation of the selective VEGF-R2 kinase inhibitor 10 (JNJ-17029259) is described in which the key precursor, 4-(5-isoxazolyl)benzonitrile, undergoes clean transformation to the corresponding cumylamine derivative with CeCL3-MeLi in THF. This high-yielding cerium mediated transformation is robust, reproducible, and readily scalable based on a requirement for the anhydrous CeCl3 to be milled and subjected to ultrasound treatment prior to addition of methyllithium.

  DOI：

  10.1021/jo7021372
• 作为产物：
  描述：

  4-(2-吗啉-4-乙基)-苯胺 、 3,5-二甲基吡唑-1-硝酸咪 以 乙腈 为溶剂， 反应 1.0h， 生成 N,N'-bis-4-(2-morpholinoethyl)phenylguanidine 、 2-[4-(2-Morpholin-4-ylethyl)phenyl]guanidine;nitric acid
  参考文献：
  名称：

  Scalable Synthesis of the VEGF-R2 Kinase Inhibitor JNJ-17029259 Using Ultrasound-Mediated Addition of MeLi−CeCl₃ to a Nitrile

  摘要：

  [GRAPHICS]The preparation of the selective VEGF-R2 kinase inhibitor 10 (JNJ-17029259) is described in which the key precursor, 4-(5-isoxazolyl)benzonitrile, undergoes clean transformation to the corresponding cumylamine derivative with CeCL3-MeLi in THF. This high-yielding cerium mediated transformation is robust, reproducible, and readily scalable based on a requirement for the anhydrous CeCl3 to be milled and subjected to ultrasound treatment prior to addition of methyllithium.

  DOI：

  10.1021/jo7021372

文献信息

• Scalable Synthesis of the VEGF-R2 Kinase Inhibitor JNJ-17029259 Using Ultrasound-Mediated Addition of MeLi−CeCl₃ to a Nitrile
  作者：Michael Reuman、Sandra Beish、Jeremy Davis、Mark J. Batchelor、Martin C. Hutchings、David F. C. Moffat、Peter J. Connolly、Ronald K. Russell

  DOI：10.1021/jo7021372

  日期：2008.2.1

  [GRAPHICS]The preparation of the selective VEGF-R2 kinase inhibitor 10 (JNJ-17029259) is described in which the key precursor, 4-(5-isoxazolyl)benzonitrile, undergoes clean transformation to the corresponding cumylamine derivative with CeCL3-MeLi in THF. This high-yielding cerium mediated transformation is robust, reproducible, and readily scalable based on a requirement for the anhydrous CeCl3 to be milled and subjected to ultrasound treatment prior to addition of methyllithium.