tert-butyl (6-amino-5-bromopyridin-3-yl)acetate | 1603830-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl (6-amino-5-bromopyridin-3-yl)acetate
• 英文别名: Tert-butyl 2-(6-amino-5-bromopyridin-3-yl)acetate
• CAS: 1603830-64-3
• 化学式: C₁₁H₁₅BrN₂O₂
• 分子量: 287.156
• InChiKey: JTAOVPNYYYHKRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (6-amino-5-bromopyridin-3-yl)acetate 在 亚硝酸特丁酯 、 palladium diacetate 、 苄基三乙基溴化铵 、 sodium hydride 、 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 1,2-二溴乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 43.0h， 生成 tert-butyl 1-(9H-pyrido[2,3-b]indol-3-yl)cyclopropanecarboxylate
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel polycyclic heteroarene ethers as PDE10A inhibitors: Part I

  摘要：

  We report analogue-based rational design and synthesis of two novel series of polycyclic heteroarenes, pyrrolo[3,2-b]quinolines and pyrido[2,3-b]indoles, tethered to a biaryl system by a methyl-, ethyl-or propyl ether as PDE10A inhibitors. A number of analogues were prepared with variable chain length and evaluated for their ability to block PDE10A enzyme using a radiometric assay. Detailed SAR analyses revealed that compounds with an ethyl ether linker are superior in potency compared to compounds with methyl or propyl ether linkers. These compounds, in general, showed poor metabolic stability in rat and human liver microsomes. The metabolic profile of one of the potent compounds was studied in detail to identify metabolic liabilities of these compounds. Structural modifications were carried out that resulted in improved metabolic stability without significant loss of potency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.054
• 作为产物：
  描述：

  tert-butyl(6-aminopyridin-3-yl)acetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以3.4 g的产率得到tert-butyl (6-amino-5-bromopyridin-3-yl)acetate
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel polycyclic heteroarene ethers as PDE10A inhibitors: Part I

  摘要：

  We report analogue-based rational design and synthesis of two novel series of polycyclic heteroarenes, pyrrolo[3,2-b]quinolines and pyrido[2,3-b]indoles, tethered to a biaryl system by a methyl-, ethyl-or propyl ether as PDE10A inhibitors. A number of analogues were prepared with variable chain length and evaluated for their ability to block PDE10A enzyme using a radiometric assay. Detailed SAR analyses revealed that compounds with an ethyl ether linker are superior in potency compared to compounds with methyl or propyl ether linkers. These compounds, in general, showed poor metabolic stability in rat and human liver microsomes. The metabolic profile of one of the potent compounds was studied in detail to identify metabolic liabilities of these compounds. Structural modifications were carried out that resulted in improved metabolic stability without significant loss of potency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.054

文献信息

• 4-SUBSTITUTED PYRROLO[2,3-B]PYRIDINE AS ERBB MODULATORS USEFUL FOR TREATING CANCER
  申请人：Lead Discovery Center GmbH

  公开号：EP3807274A1

  公开（公告）日：2021-04-21
• [EN] 4-SUBSTITUTED PYRROLO[2,3-B]PYRIDINE AS ERBB MODULATORS USEFUL FOR TREATING CANCER<br/>[FR] PYRROLO[2,3-B]PYRIDINE SUBSTITUÉE EN POSITION 4 EN TANT QUE MODULATEURS D'ERBB UTILES POUR LE TRAITEMENT DU CANCER
  申请人：LEAD DISCOVERY CENTER GMBH

  公开号：WO2020039060A1

  公开（公告）日：2020-02-27

  The present invention relates to certain 4-substituted 1H-pyrrolo[2,3-b]pyridine compounds of the formula (I) and pharmaceutically acceptable salts thereof. These compounds is useful in the treatment or prevention of a disease or medical condition mediated through certain mutated forms of ErbB receptor, especially of Exon20 Her2 and EGFR mutations.