5-氯-2-氧化吲哚-1-甲酰胺 | 100599-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-氯-2-氧化吲哚-1-甲酰胺
• 英文名称: 5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide
• 英文别名: 5-chloro-2-oxo-3H-indole-1-carboxamide；5-chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide；5-chlorooxindole-1-carboxamide
• CAS: 100599-06-2
• 化学式: C₉H₇ClN₂O₂
• 分子量: 210.62
• InChiKey: WGRHBRAKCHCGER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-噻吩甲酰氯 、 5-氯-2-氧化吲哚-1-甲酰胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88.1%的产率得到5-氯-2-氧代-3-(噻吩-2-羰基)-3H-吲哚-1-甲酰胺
  参考文献：
  名称：

  Synthesis of Tenidap: An Improved Process for the Preparation of 5-Chloro-2-oxindole-1-carboxamide

  摘要：

  An industrially viable, robust, and economic process is developed for Tenidap sodium and its important intermediate 5-chloro-2-oxindole-1-carboxamide. Use of inorganic cyanates, in place of organic isocyanates, makes the process simple and commercially viable. The advantage of using acetic anhydride and sodium acetate over reported reagents such as trifluoroacetic acid and its anhydride on industrial scale is described. Drastic reduction of DMAP in the final step and overall improvement of yields makes the process economical.

  DOI：

  10.1021/op000082b
• 作为产物：
  描述：

  5-氯氧化吲哚 在 sodium acetate 、 乙酸酐 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 9.0h， 生成 5-氯-2-氧化吲哚-1-甲酰胺
  参考文献：
  名称：

  Synthesis of Tenidap: An Improved Process for the Preparation of 5-Chloro-2-oxindole-1-carboxamide

  摘要：

  An industrially viable, robust, and economic process is developed for Tenidap sodium and its important intermediate 5-chloro-2-oxindole-1-carboxamide. Use of inorganic cyanates, in place of organic isocyanates, makes the process simple and commercially viable. The advantage of using acetic anhydride and sodium acetate over reported reagents such as trifluoroacetic acid and its anhydride on industrial scale is described. Drastic reduction of DMAP in the final step and overall improvement of yields makes the process economical.

  DOI：

  10.1021/op000082b
• 作为试剂：
  描述：

  5-氯-2-氧化吲哚-1-甲酰胺 、 4,5-二溴-2-噻吩羰酰氯 在 5-氯-2-氧化吲哚-1-甲酰胺 作用下， 以40的产率得到(3Z)-5-chloro-3-[(4,5-dibromothiophen-2-yl)-hydroxymethylidene]-2-oxoindole-1-carboxamide
  参考文献：
  名称：

  Process for making 3-aroyl-2-oxindole-1-carboxamides

  摘要：

  制备抗炎症3-芳酰基-2-氧喹啉-1-羧酰胺的过程是通过对3-(溴或碘芳酰基)-2-氧喹啉-1-羧酰胺进行还原去溴或去碘。

  公开号：

  US05059693A1

文献信息

• Convenient synthesis of 3-unsubstituted oxindole-1-carboxamides
  作者：Márta Porcs-Makkay、Balázs Volk、Eszter Kókai、Gyula Simig

  DOI：10.1016/j.tet.2011.12.027

  日期：2012.2

  elaborated for the synthesis of 3-unsubstituted oxindole-1-carboxamides starting from the easily available 1,3-bis(phenoxycarbonyl)oxindoles. Selective amidation of the N-phenoxycarbonyl moiety and subsequent removal of the C(3)-phenoxycarbonyl moiety furnished the title compounds, which are useful building blocks for further functionalization. Besides the novel methodologies, several new representatives

  由N-或C（3）-3个未取代的羟吲哚的质子化形成的介观阴离子的多重反应性阻碍了将取代基选择性引入到氮原子上。从容易获得的1，3-双（苯氧羰基）恶吲哚开始，已经详细阐述了一种方便适用的反应顺序，用于合成3-未取代的羟吲哚-1-甲酰胺。N-苯氧羰基部分的选择性酰胺化和随后的C（3）-苯氧羰基部分的除去提供了标题化合物，其是用于进一步官能化的有用的结构单元。除了新颖的方法外，下面还将介绍该有价值的化合物家族及其中间体的几个新代表。
• New Practical Synthesis of Tenidap
  作者：Márta Porcs-Makkay、Gyula Simig

  DOI：10.1021/op990067a

  日期：2000.1.1

  The development of a new, practical synthesis to tenidap is described. N,O-Dialkoxy(aryloxy)carbonylation of 5-chloro-2-oxo-2,3-dihydroindole, followed by removal of the O-alkoxy(aryloxy)carbonyl group gave 1-[alkoxy(aryloxy)carbonyl]-5-chloro-2-oxo-2,3-dihydroindoles in good yields. The latter compounds were thenoylated in the 3-position. The role of DMAP in the acylation reaction is discussed. The

  描述了一种新的实用合成替尼达普的开发。5-氯-2-氧代-2,3-二氢吲哚的N,O-二烷氧基(芳氧基)羰基化，然后除去O-烷氧基(芳氧基)羰基得到1-[烷氧基(芳氧基)羰基]-5-氯-2-氧代-2,3-二氢吲哚的收率良好。后一种化合物在 3 位进行了酚化。讨论了 DMAP 在酰化反应中的作用。在溶液和固相中研究了 thenoylated 产物及其烯醇盐的结构。5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole 的氨解以高产率提供相应的 1-carbamoyl 衍生物 (tenidap)。相应的 1-乙氧基和 1-甲氧基羰基衍生物不能类似地转化为替尼达；
• Process for making 2-oxindole-1-carboxamides and intermediates therefor
  申请人：Pfizer Inc.

  公开号：US04652658A1

  公开（公告）日：1987-03-24

  Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with chlorosulfonyl isocyanate to produce novel N-chlorosulfonyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as intermediates for analgesic and antiinflammatory agents.

  通过2-氧吲哚与氯磺酰异氰酸酯反应制备2-氧吲哚-1-羧酰胺，生成新型N-氯磺酰基-2-氧吲哚-1-羧酰胺，然后水解成为2-氧吲哚-1-羧酰胺，该化合物可作为镇痛和抗炎制剂的中间体。
• 3-substituted-2-oxindole derivatives
  申请人：Pfizer Inc.

  公开号：US05047554A1

  公开（公告）日：1991-09-10

  This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.

  本发明涉及新型的3-取代-2-氧吲哚衍生物，它们是前列腺素H.sub.2合酶、5-脂氧合酶和白细胞介素-1生物合成的抑制剂。本发明的化合物本身是前列腺素H.sub.2合酶和白细胞介素-1生物合成的抑制剂，并可用于治疗慢性炎症性疾病的镇痛、抗炎和抗关节炎剂。本发明还涉及包括所述3-取代-2-氧吲哚衍生物的药物组合物；抑制前列腺素H.sub.2合酶和白细胞介素-1生物合成的方法；以及使用该化合物治疗哺乳动物的慢性炎症性疾病。此外，本发明还涉及某些新型羧酸，它们是制备本发明的3-取代-2-氧吲哚衍生物的中间体，以及制备该3-取代-2-氧吲哚衍生物的方法。
• 3-Substituted 2-oxindole-1-carboxamides as analgesic and
  申请人：Pfizer Inc.

  公开号：US04556672A1

  公开（公告）日：1985-12-03

  Certain new 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and anti-inflammatory agents in mammalian subjects. In particular, the compounds of the invention are useful for ameliorating or eliminating pain in human subjects recovering from surgery or trauma, and in alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.

  某些新的2-氧化吲哚-1-羧酰胺化合物，在3-位置具有酰基取代基，是环氧合酶(CO)和脂氧合酶(LO)酶的抑制剂，并且在哺乳动物主体中作为镇痛和抗炎药物非常有用。特别是，本发明的化合物对于减轻或消除人体手术或创伤恢复过程中的疼痛，并缓解慢性疾病（如类风湿性关节炎和骨关节炎）的症状在人体中非常有用。