3-amino-4-[(1-methylpiperidin-4-yl)oxy]thieno[2,3-b]pyridine-2-carboxamide | 1630042-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-amino-4-[(1-methylpiperidin-4-yl)oxy]thieno[2,3-b]pyridine-2-carboxamide
• 英文别名: 3-Amino-4-(1-methylpiperidin-4-yl)oxythieno[2,3-b]pyridine-2-carboxamide；3-amino-4-(1-methylpiperidin-4-yl)oxythieno[2,3-b]pyridine-2-carboxamide
• CAS: 1630042-14-6
• 化学式: C₁₄H₁₈N₄O₂S
• 分子量: 306.389
• InChiKey: WWJSDWDCEWGPEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-chloro-3-cyano-4-hydroxypyridine 、 1-甲基-4-哌啶醇 在 水 、 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.08h， 生成 3-amino-4-[(1-methylpiperidin-4-yl)oxy]thieno[2,3-b]pyridine-2-carboxamide
  参考文献：
  名称：

  An Efficient Method for the Preparation of 4-Alkoxy-substituted Thieno[2,3-b]pyridines

  摘要：

  An efficient method for the preparation of 4-alkoxy-substituted thieno[2,3-b]pyridines is described. The key intermediates, 4-alkoxy-2-chloro-3-cyanopyridines, were synthesized from a variety of alcohols by nucleophilic substitution with 3-cyano-2,4-dichloropyridine or by Mitsunobu reaction with 2-chloro-4-hydroxynicotinonitrile. Subsequent reaction of 4-alkoxy-2-chloro-3-cyanopyridines with 2-(acetylthio)acetamide under basic conditions provided 4-alkoxy-substituted thieno[2,3-b]pyridines in fair to good yields.

  DOI：

  10.3987/com-14-12986

文献信息

• Synthesis and structure-activity relationship of 4-alkoxy-thieno[2,3-b]pyridine derivatives as potent alkaline phosphatase enhancers for osteoporosis treatment
  作者：Keiji Saito、Tsuyoshi Shinozuka、Akira Nakao、Toshihiro Kiho、Tomonori Kunikata、Takeshi Shiiki、Yoko Nagai、Satoru Naito

  DOI：10.1016/j.bmcl.2019.05.014

  日期：2019.7

  The synthesis and structure-activity relationships of a novel series of 3-aminothieno[2,3-b]pyridine-2-carbox-amides were explored. Our efforts were focused on modifying the C-4 substituent of the thienopyridine ring to develop orally available bone anabolic agents. 4-Alkoxy derivatives were found to be novel ALPase enhancers without inhibitory effect on P450 activity. Among these derivatives, compound 6k was orally administered to ovariectomized rats, and it was found to significantly improve areal bone mineral density at a dose of 30 mg/kg/day.
• An Efficient Method for the Preparation of 4-Alkoxy-substituted Thieno[2,3-b]pyridines
  作者：Tsuyoshi Shinozuka、Keiji Saito、Satoru Naito

  DOI：10.3987/com-14-12986

  日期：——

  An efficient method for the preparation of 4-alkoxy-substituted thieno[2,3-b]pyridines is described. The key intermediates, 4-alkoxy-2-chloro-3-cyanopyridines, were synthesized from a variety of alcohols by nucleophilic substitution with 3-cyano-2,4-dichloropyridine or by Mitsunobu reaction with 2-chloro-4-hydroxynicotinonitrile. Subsequent reaction of 4-alkoxy-2-chloro-3-cyanopyridines with 2-(acetylthio)acetamide under basic conditions provided 4-alkoxy-substituted thieno[2,3-b]pyridines in fair to good yields.