{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}boronic acid | 1310556-95-6

• 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: {1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}boronic acid
• 英文别名: [1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-4-yl]boronic acid
• CAS: 1310556-95-6
• 化学式: C₁₄H₁₃BN₂O₄S
• 分子量: 316.145
• InChiKey: DKLLRKCRTYNUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}boronic acid 、 [1-[2-chloro-6-[(3R)-3-methylmorpholin-4-yl]-pyrimidin-4-yl]cyclopropyl](imino)methyloxo-λ6-sulfane hydrochloride 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 AZD6738
  参考文献：
  名称：

  Development and Scale-up of a Route to ATR Inhibitor AZD6738

  摘要：

  AZD6738 is currently being tested in multiple phase I/II trials for the treatment of cancer. Its structure, comprising a pyrimidine core decorated with a chiral morpholine, a cyclopropyl sulfoximine, and an azaindole, make it a challenging molecule to synthesize on a large scale. We describe the evolution of the chemical processes, following the manufacture of AZD6738 from the initial scale-up through to multikilos on plant scale. During this evolution, we developed a biocatalytic process to install the sulfoxide with high enantioselectivity, followed by introduction of the cyclopropyl group first in batch, then in a continuous flow plate reactor, and finally through a series of continuous stirred tank reactors. The final plant scale process to form AZD6738 was operated on 46 kg scale with an overall yield of 18%. We discuss the impurities formed throughout the process and highlight the limitations of this route for further scale-up.

  DOI：

  10.1021/acs.oprd.9b00075
• 作为产物：
  描述：

  4-溴-7-氮杂吲哚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 {1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}boronic acid
  参考文献：
  名称：

  Development and Scale-up of a Route to ATR Inhibitor AZD6738

  摘要：

  AZD6738 is currently being tested in multiple phase I/II trials for the treatment of cancer. Its structure, comprising a pyrimidine core decorated with a chiral morpholine, a cyclopropyl sulfoximine, and an azaindole, make it a challenging molecule to synthesize on a large scale. We describe the evolution of the chemical processes, following the manufacture of AZD6738 from the initial scale-up through to multikilos on plant scale. During this evolution, we developed a biocatalytic process to install the sulfoxide with high enantioselectivity, followed by introduction of the cyclopropyl group first in batch, then in a continuous flow plate reactor, and finally through a series of continuous stirred tank reactors. The final plant scale process to form AZD6738 was operated on 46 kg scale with an overall yield of 18%. We discuss the impurities formed throughout the process and highlight the limitations of this route for further scale-up.

  DOI：

  10.1021/acs.oprd.9b00075

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2011067364A1

  公开（公告）日：2011-06-09

  The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I): and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

  这项发明涉及某些新颖化合物。具体而言，该发明涉及具有以下结构的化合物（I）及其盐。该发明的化合物是PI3-激酶活性的抑制剂。
• Indazole derivatives for use in the treatment of influenza virus infection
  申请人：Hamblin Julie Nicole

  公开号：US09326987B2

  公开（公告）日：2016-05-03

  The present invention is directed to compounds for use in the treatment or prevention of influenza virus infection.

  本发明涉及用于治疗或预防流感病毒感染的化合物。
• NOVEL COMPOUNDS
  申请人：Baldwin Ian Robert

  公开号：US20120238559A1

  公开（公告）日：2012-09-20

  The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I): and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

  本发明涉及某些新型化合物。具体而言，本发明涉及式（I）的化合物及其盐。本发明的化合物是PI3-激酶活性的抑制剂。
• Novel Use
  申请人：Baldwin Ian Robert

  公开号：US20130165433A1

  公开（公告）日：2013-06-27

  The present invention is directed to compounds for use in the treatment or prevention of influenza virus infection.

  本发明涉及用于治疗或预防流感病毒感染的化合物。