6-methoxy-2-methylbenzo[b]thiophene-3-carboxylic acid | 854515-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-methoxy-2-methylbenzo[b]thiophene-3-carboxylic acid
• 英文别名: 6-methoxy-2-methyl-1-benzothiophene-3-carboxylic acid
• CAS: 854515-01-8
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: QOWXSQNFVNTGQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-methylbenzo[b]thiophene-3-carboxylic acid 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 6-甲氧基-N,2-二甲基-1-苯并噻吩-3-甲酰胺
  参考文献：
  名称：

  Development of a Scalable Synthesis to VEGFR Inhibitor AG-28262

  摘要：

  The synthesis of N,2-dimethyl-6-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxamide (1, AG-28262) on kilogram scale is described. Initial syntheses of key components 2 and 3 worked well on laboratory scale but had significant drawbacks for larger-scale manufacture. Therefore, new routes to these two key fragments were developed and demonstrated to synthesize kilogram quantities. Key steps involve a two-step thiophenol alkylation/cyclization protocol to synthesize 2 in a convergent manner. A difficult Pd-mediated coupling to produce 3 was replaced with a more scalable stepwise imidazole synthesis. Key rationale for the new routes are discussed.

  DOI：

  10.1021/op0502396
• 作为产物：
  描述：

  3-(3-methoxyphenylthio)-2-oxobutanoic acid 在 硫酸 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 6.23h， 以55%的产率得到6-methoxy-2-methylbenzo[b]thiophene-3-carboxylic acid
  参考文献：
  名称：

  WO2007/26221

  摘要：

  公开号：

文献信息

• [EN] NOVEL QUINOLINE DERIVATIVES<br/>[FR] DERIVES NOUVEAUX DE QUINOLEINE
  申请人：PFIZER

  公开号：WO2005063739A1

  公开（公告）日：2005-07-14

  The invention relates to compounds represented by Formula (I): and to pharmaceutically acceptable salts or solvates of said compounds, wherein each of A, R3-8, X3, X5, m, and n are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).

  该发明涉及由式(I)表示的化合物，以及所述化合物的药学上可接受的盐或溶剂化合物，其中A、R3-8、X3、X5、m和n在此处被定义。该发明还涉及含有式(I)化合物的药物组合物，以及通过给予式(I)化合物治疗哺乳动物的增生性疾病的方法。
• Novel quinoline derivatives
  申请人：Hong Yufeng

  公开号：US20050137395A1

  公开（公告）日：2005-06-23

  The invention relates to compounds represented by Formula (I): and to pharmaceutically acceptable salts or solvates of said compounds, wherein each of A, R 3-8 , X 3 , X 5 , m, and n are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).

  本发明涉及由公式(I)所代表的化合物，以及该化合物的药学上可接受的盐或溶剂，其中A、R3-8、X3、X5、m和n均在此定义。本发明还涉及含有公式(I)化合物的制药组合物，以及通过给哺乳动物注射公式(I)化合物来治疗增生性疾病的方法。
• NOVEL QUINOLINE DERIVATIVES
  申请人：Hong Yufeng

  公开号：US20090069316A1

  公开（公告）日：2009-03-12

  The invention relates to compounds represented by Formula (I): and to pharmaceutically acceptable salts or solvates of said compounds, wherein each of A, R 3-8 , X 3 , X 5 , m, and n are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).

  该发明涉及由公式（I）表示的化合物，以及该化合物的药学上可接受的盐或溶剂，其中在此定义了A、R3-8、X3、X5、m和n中的每个。该发明还涉及包含公式（I）化合物的药物组合物，以及通过给予公式（I）化合物来治疗哺乳动物的过度增殖性疾病的方法。
• Quinoline derivatives
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：US07381824B2

  公开（公告）日：2008-06-03

  The invention relates to compounds represented by Formula (I): and to pharmaceutically acceptable salts or solvates of said compounds, wherein each of A, R3-8, X3, X5, m, and n are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).

  本发明涉及由公式（I）表示的化合物及其药学上可接受的盐或溶剂，其中A、R3-8、X3、X5、m和n在此定义。本发明还涉及含有公式（I）化合物的制药组合物，以及通过给哺乳动物施用公式（I）化合物治疗增生性疾病的方法。
• US7381824B2
  申请人：——

  公开号：US7381824B2

  公开（公告）日：2008-06-03