N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide | 478081-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
• 英文别名: isozaleplon；N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide；N-[3-(3-cyanopyrazolo[1,5]pyrimidin-5-yl)phenyl]-N-ethylacetamide
• CAS: 478081-98-0
• 化学式: C₁₇H₁₅N₅O
• 分子量: 305.339
• InChiKey: ZMUMYMWAIXXLIY-UHFFFAOYSA-N

物化性质

• 熔点：
  203-205 °C
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯吡唑并[1,5-a]嘧啶-3-甲腈 、 N-ethyI-N-(3-(4,4,5,5-tetramethyI-1,3,2-dioxaboroIan-2-yl)phenyI)acetamide 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以81.9%的产率得到N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
  参考文献：
  名称：

  Synthetic Studies Connected with the Preparation of N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide, a Zaleplon Regioisomer

  摘要：

  N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethyl-acetamide, a principal impurity of zaleplon, is prepared by Suzuki-Miyaura cross coupling reaction of the corresponding boronic acid and/or boronates with 5-chloropyrazolo[1,5-a]pyrimidin-3-carbonitrile (7). Various methods of preparation of both components are described, as well as approaches based on the final modification of the 5-(3-aminophenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile moiety prepared by Suzuki-Miyaura cross coupling. All the prepared compounds were unambiguouesly identified by NMR techniques. Spectral characteristics (IR, UV, MS) of these compounds are also given.

  DOI：

  10.3987/com-09-s(s)129

文献信息

• [EN] TWO-PHASE METHOD FOR THE SYNTHESIS OF SELECTED PYRAZOLOPYRIMIDINES<br/>[FR] PROCEDE EN DEUX PHASES DESTINE A LA SYNTHESE DE PYRAZOLOPYRIMIDINES SELECTIONNES
  申请人：MALLINCKRODT INC

  公开号：WO2005070931A1

  公开（公告）日：2005-08-04

  An improved method of making a substituted pyrazolopyrimidine. The method comprises reacting a aminopyrazole compound or a salt thereof with a substituted 1-oxo-2-propenyl-arene(-heterocycle) or a salt thereof under acidic conditions in a reaction medium including a two-phase mixture of an aqueous solution and a water-immiscible organic liquid. Specific substituted pyrazolopyrimidines include N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide and N-methyl-N-(3-3-[2-thienylcarbonyl]-pyrazolo[1, 5-a]-pyrimidin-7-yl}phenyl)acetamide.

  一种改进的制备取代吡唑吡咯嘧啶的方法。该方法包括在酸性条件下，将氨基吡唑化合物或其盐与取代的1-氧代-2-丙烯基芳烃（-杂环）或其盐在包括水溶液和水不相溶有机液体的两相混合物中反应。特定的取代吡唑吡咯嘧啶包括N-[3-(3-氰基吡唑[1,5-a]嘧啶-7-基)苯基]-N-乙醋胺和N-甲基-N-(3-3-[2-噻吩甲酰]-吡唑[1,5-a]-嘧啶-7-基}苯基)乙醋胺。
• Process for purifying N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide (zaleplon) and crystalline forms of zaleplon accessible with the process
  申请人：Feher Erika

  公开号：US06852858B2

  公开（公告）日：2005-02-08

  Zaleplon can be separated from a regioisomer impurity by crystallization from selected solvents or by adding an anti-solvent to a solution of zaleplon and the regioisomer. Zaleplon crystalline Forms II, III, IV, and V are useful for the treatment of insomnia. These crystalline Forms are described along with processes for making them v crystallization from selected solvents.

  Zaleplon可以通过从选择的溶剂中结晶或通过向Zaleplon和异构体的溶液中加入抗溶剂来与区域异构体杂质分离。 Zaleplon结晶形式II，III，IV和V可用于治疗失眠。 这些结晶形式以及从选择的溶剂中结晶制备它们的过程被描述。
• Process for the production of N-[3-(3-cyanopyrazolo[1,5-a] pyrimidin-7-yl) phenyl]-N-ethylacetamide (zaleplon)
  申请人：——

  公开号：US20030040522A1

  公开（公告）日：2003-02-27

  The present invention provides a process for the production of N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide (zaleplon), an active ingredient that is approved for the treatment of insomnia. The process involves reacting N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylacetamide or a salt thereof with 3-amino-4-cyanopyrazole or a salt thereof under acidic conditions in a reaction medium comprising a mixture of water and a water-miscible organic compound.

  本发明提供一种生产N-[3-(3-氰基吡唑并[1,5-a]嘧啶-7-基)苯基]-N-乙酰乙酸乙酯（扎来普隆），一种用于治疗失眠症的有效成分的方法。该方法涉及在反应介质中，通过在水和一种水溶性有机化合物的混合物中在酸性条件下反应N-[3-（3-二甲氨基）-1-氧代-2-丙烯基]苯基]-N-乙酰乙酸乙酯或其盐与3-氨基-4-氰基吡唑或其盐反应。
• N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide and crystalline forms of zaleplon
  申请人：Korodi Ferenc

  公开号：US20050032818A1

  公开（公告）日：2005-02-10

  Zaleplon crystalline Forms II, III, IV and V are useful for the treatment of insomnia. These crystalline Forms are described along with processes for making them by crystallization from selected solvents. A regioisomer of zaleplon is useful as a reference standard for monitoring the composition of production batches of zaleplon.

  Zaleplon的II、III、IV和V结晶形式对于治疗失眠是有用的。这些结晶形式与通过从选择的溶剂中结晶制备它们的过程一起描述。Zaleplon的一个异构体可用作参考标准，用于监测Zaleplon生产批次的组成。
• [EN] A PROCESS FOR THE PREPARATION OF ZALEPLON<br/>[FR] PROCEDE DE PREPARATION DE ZALEPLON
  申请人：ADAMED SP ZOO

  公开号：WO2003095456A1

  公开（公告）日：2003-11-20

  The invention relates to a process for the preparation of zaleplon (N-[3(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethyl-acetamide) in the reaction of 3-dimethylamino-1-(3-N-ethyl-N-acetylaminophenyl)-2-propen-1-one with 3-aminopyrazole-4-carbonitrile, which comprises carrying out said reaction in an aqueous solution of formic acid at formic acid concentrations in the range of 20-80% (w/w). Zaleplon is useful as an anxiolytic, a sedactive and a skeletal muscle relaxant.

  本发明涉及一种制备扎来普隆（N-[3(3-氰基吡唑[1,5-a]嘧啶-7-基)苯基]-N-乙基乙酰胺）的方法，其中在3-二甲氨基-1-(3-N-乙基-N-乙酰氨基苯基)-2-丙酮与3-氨基吡唑-4-碳腈反应中，在甲酸水溶液中进行该反应，甲酸浓度在20-80%（w/w）范围内。扎来普隆可用作抗焦虑药、镇静剂和骨骼肌松弛剂。