6-溴-4-乙基喹唑啉 | 602330-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-溴-4-乙基喹唑啉
• 英文名称: 6-bromo-4-ethylquinazoline
• 英文别名: 6-Bromo-4-ethylquinazoline
• CAS: 602330-33-6
• 化学式: C₁₀H₉BrN₂
• 分子量: 237.099
• InChiKey: AIMIGFJHYPDTEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-溴-4-乙基喹唑啉 在 lithium carbonate 、 N-氟代双苯磺酰胺 作用下， 以 乙腈 为溶剂， 以91%的产率得到6-Bromo-4-(1-fluoroethyl)quinazoline
  参考文献：
  名称：

  与二苯磺酰胺衍生物直接进行杂苄基氟化，二氟化和三氟甲硫基化†

  摘要：

  具有单或二氟烷基的杂环支架的功能化提供了调节药物p K a，影响效价和膜通透性以及减弱新陈代谢的独特机会。尽管已经取得了在杂环上添加氟代烷基自由基的进展，但是相对而言，尚没有直接进行C（sp 3）–H杂苄基氟化反应的研究。在这里，我们证明了使用便利方法的一系列烷基杂环的单氟化和二氟化反应，该方法依赖于亲电氟化剂N-氟苯磺酰亚胺的瞬时磺酰化作用。我们还报告了杂苄基三氟甲基硫醇化和18 F-氟化，为后期C（sp 3）–药物线索的H功能化和放射性示踪剂的发现。

  DOI：

  10.1039/c8sc01221k
• 作为产物：
  描述：

  2-氨基-5-溴苯甲腈 在 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 6-溴-4-乙基喹唑啉
  参考文献：
  名称：

  EP3569596

  摘要：

  公开号：

文献信息

• 1,2,4-TRIAZINE-3-AMINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF IN MEDICINE
  申请人：Jiangsu Hengrui Medicine Co. Ltd.

  公开号：EP3569596A1

  公开（公告）日：2019-11-20

  The present invention relates to a 1,2,4-triazine-3-amine derivative, a preparation therefor, and use thereof in medicine. Specifically, the present invention relates to a 1,2,4-triazine-3-amine derivative as represented by general formula (I), a preparation method therefor, a pharmaceutical composition comprising the derivative, and use thereof as a therapeutic agent, in particular as an A2a receptor antagonist, and use thereof in the preparation of a medicament for treating a condition or disorder that is ameliorated by means of inhibition of the A2a receptor, each substituent in general formula (I) being same as defined in the description.

  本发明涉及一种1,2,4-三嗪-3-胺衍生物、其制备方法及其在医药中的用途。具体地说，本发明涉及通式（I）所代表的1,2,4-三嗪-3-胺衍生物、其制备方法、包含该衍生物的药物组合物及其作为治疗剂的用途，特别是作为A2a受体拮抗剂的用途，以及其在制备用于治疗通过抑制A2a受体而改善的病症或紊乱的药物中的用途，通式（I）中的各取代基与描述中所定义的相同。
• 1,2,4-triazine-3-amine derivative, preparation method therefor, and use thereof in medicine
  申请人：Jiangsu Hengrui Medicine Co., Ltd.

  公开号：US11014904B2

  公开（公告）日：2021-05-25

  A 1,2,4-triazine-3-amine derivative, a preparation therefor, and use thereof in medicine are provided. Specifically, a 1,2,4-triazine-3-amine derivative as represented by general formula (I), a preparation method therefor, a pharmaceutical composition containing the derivative, and use thereof as a therapeutic agent, in particular as an A2a or A2b receptor antagonist, and use thereof in the preparation of a medicament for treating a condition or disorder that is ameliorated by means of inhibition of the A2a or A2b receptor are provided. Each substituent in general formula (I) is defined in the description.

  本发明提供了一种 1,2,4-三嗪-3-胺衍生物、其制备方法及其在医药中的用途。 具体地说，本发明提供了通式（I）所代表的1,2,4-三嗪-3-胺衍生物、其制备方法、含有该衍生物的药物组合物及其作为治疗剂的用途，特别是作为A2a或A2b受体拮抗剂的用途，以及其在制备用于治疗通过抑制A2a或A2b受体而改善的病症或紊乱的药物中的用途。 通式(I)中各取代基的定义见说明。
• [EN] 1,2,4-TRIAZINE-3-AMINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF IN MEDICINE<br/>[FR] DÉRIVÉ DE 1,2,4-TRIAZINE-3-AMINE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION EN MÉDECINE<br/>[ZH] 1,2,4-三嗪-3-胺类衍生物、其制备方法及其在医药上的应用
  申请人：JIANGSU HENGRUI MEDICINE CO

  公开号：WO2018130184A1

  公开（公告）日：2018-07-19

  本发明涉及1,2,4-三嗪-3-胺类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的1,2,4-三嗪-3-胺类衍生物、其制备方法及含有该衍生物的药物组合物以及其作为治疗剂，特别是作为A2a受体拮抗剂的用途和在制备用于治疗通过对A2a受体的抑制而改善的病况或病症的药物中的用途，其中通式(I)的各取代基与说明书中的定义相同。
• A Practical Synthesis of 6-[2-(2,5-Dimethoxyphenyl)ethyl]-4-ethylquinazoline and the Art of Removing Palladium from the Products of Pd-Catalyzed Reactions
  作者：Kurt Königsberger、Guang-Pei Chen、Raeann R. Wu、Michael J. Girgis、Kapa Prasad、Oljan Repič、Thomas J. Blacklock

  DOI：10.1021/op034072x

  日期：2003.9.1

  A concise large-scale synthesis of 1, a new antimitotic agent is described. The key step was a one-pot Sonogashira cross-coupling of an aryl halide with a heteroaryl halide through an acetylene using the readily available 2-methyl-3-butyn-2-ol (7). An innovative approach for palladium removal was designed and successfully scaled-up on a multikilogram scale. The product was crystallized from the crude reaction mixture while keeping the residual palladium in the mother liquor by using Pd-scavenging agents such as N-acetylcysteine or thiourea.
• Design of New Reaction Conditions for the Sugasawa Reaction Based on Mechanistic Insights
  作者：Kapa Prasad、George T. Lee、Apurva Chaudhary、Michael J. Girgis、James W. Streemke、Oljan Repič

  DOI：10.1021/op0340659

  日期：2003.9.1

  A process to prepare 2-propionyl-4-bromoaniline by ortho acylation of 4-bromoaniline under Sugasawa conditions was developed. Upon scale-up in a pilot plant, the process gave lower yields than in the laboratory in four out of five plant runs. Analysis of the pilot-plant data, in conjunction with reaction calorimetric experiments, showed that expulsion of HCl from the reaction medium was key for obtaining high product yields. New reaction conditions were subsequently developed for carrying out ortho acylation of 4-bromoaniline (1). The reaction mixture containing aniline/BCl3/AlCl3/C2H5CN was added to a refluxing solution of toluene to allow for substantial HCl expulsion and thus obtain the optimum yield of the desired product. Aniline hydrochlorides were also shown to be suitable starting materials under these conditions. Mechanistic implications of these findings are discussed. The new reaction conditions significantly increased the yield.