methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate | 1236722-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate
• 英文别名: methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxylate；methyl 5-[4-[4-(5-cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxylate；Vilazodone methyl ester；methyl 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxylate
• CAS: 1236722-93-2
• 化学式: C₂₇H₂₈N₄O₃
• 分子量: 456.544
• InChiKey: NAXYPJOGTVVGFR-UHFFFAOYSA-N

物化性质

• 沸点：
  681.1±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 以98.5%的产率得到维拉佐酮
  参考文献：
  名称：

  [EN] PREPARATION OF VILAZODONE HYDROCHLORIDE CRYSTALLINE FORM IV
  [FR] PRÉPARATION DE CHLORHYDRATE DE VILAZODONE SOUS FORME CRISTALLINE IV

  摘要：

  本文提供了一种改进的、商业可行的、一致可再现的工艺，用于制备高度纯净的Vilazodone盐酸盐晶型IV，该晶型不含其他多晶形式和不想要的溶剂化形式。同时，本文还提供了一种高度纯净且稳定的Vilazodone盐酸盐晶型IV，基本上不含其他固态形式。使用本文所披露的工艺制备的高度纯净的Vilazodone盐酸盐晶型IV，可用于制药组合物，其D(90)粒径小于或等于约100微米。

  公开号：

  WO2015037010A1
• 作为产物：
  描述：

  3-(4-羟基丁基)-1H-吲哚-5-甲腈 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate
  参考文献：
  名称：

  [EN] IMPROVED PROCESS FOR PREPARING BENZOFURAN-2-CARBOXAMIDE DERIVATIVES
  [FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE DÉRIVÉS DE BENZOFURAN-2-CARBOXAMIDE

  摘要：

  公开号：

  WO2014006637A3

文献信息

• PROCESS FOR PREPARING VILAZODONE HYDROCHLORIDE
  申请人：Ferrari Massimo

  公开号：US20130225818A1

  公开（公告）日：2013-08-29

  The present invention relates, in a first aspect, to a process preparing vilazodone hydrochloride that comprises the reaction of 3-(4-chloro-1-hydroxy-butyl)-1H-indol-5-carbonitrile with 5-piperazin-1-yl-benzofuran-2-carboxylate methyl hydrochloride with the formation of a 1,4-piperazine, with subsequent dehydration, hydrogenation and treatment with ammonia, to obtain vilazodone in free base form that is then converted into the hydrochloride thereof.

  本发明涉及一种制备维拉唑酮盐酸盐的过程，其中包括将3-(4-氯-1-羟基丁基)-1H-吲哚-5-羧腈与5-哌嗪-1-基苯并呋喃-2-羧酸甲酯反应，形成1,4-哌嗪，随后脱水、加氢并用氨处理，以获得维拉唑酮的游离碱形式，然后将其转化为盐酸盐形式。
• IMPROVED PROCESS FOR PREPARING BENZOFURAN-2-CARBOXAMIDE DERIVATIVES
  申请人：SYMED LABS LIMITED

  公开号：US20150322030A1

  公开（公告）日：2015-11-12

  Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.

  本文提供了一种新的、商业上可行且具有工业优势的方法，用于高产率和高纯度制备苯并呋喃-2-羧酰胺衍生物及其中间体，或其药学上可接受的盐。特别提供了一种新的、商业上可行且具有工业优势的方法，用于高产率和高纯度制备维拉唑酮或其药学上可接受的盐。本文还提供了一种改进的、商业上可行的方法，使用新的中间体化合物3-(4-羟基丁酰基)-1H-吲哚-5-碳腈，高产率和高纯度地制备3-(4-羟基丁基)-1H-吲哚-5-碳腈。
• PROCESS FOR PREPARING BENZOFURAN-2-CARBOXAMIDE DERIVATIVES
  申请人：SYMED LABS LIMITED

  公开号：US20170267655A1

  公开（公告）日：2017-09-21

  Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.

  本文提供了一种新颖、商业可行和工业优势的过程，用于制备苯并呋喃-2-羧酰胺衍生物及其中间体，或其药用可接受盐，产率和纯度高。本文特别提供了一种新颖、商业可行和工业优势的过程，用于制备维拉唑酮或其药用可接受盐，产率和纯度高。本文还提供了一种改进的、商业可行的过程，用于利用新的中间化合物3-(4-羟基丁酰基)-1H-吲哚-5-碳腈，高产高纯地制备3-(4-羟基丁基)-1H-吲哚-5-碳腈。
• Process for preparing benzofuran-2-carboxamide derivatives
  申请人：SYMED LABS LIMITED

  公开号：US09315456B2

  公开（公告）日：2016-04-19

  Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.

  本文提供了制备苯并呋喃-2-羧酰胺衍生物及其中间体或其药学上可接受的盐的新颖、商业化和工业上优越的工艺，其产率和纯度高。特别提供了一种制备维拉唑酮或其药学上可接受的盐的新颖、商业化和工业上优越的工艺，其产率和纯度高。本文还提供了一种改进的、商业化的制备3-(4-羟基丁基)-1H-吲哚-5-碳腈的工艺，使用新颖的中间体化合物3-(4-羟基丁酰基)-1H-吲哚-5-碳腈，产率和纯度高。
• Process for preparing vilazodone hydrochloride
  申请人：ERREGIERRE S.p.A.

  公开号：EP2647625B1

  公开（公告）日：2015-10-21