(-)-dimethyl-{2-[3-((R)-1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine | 873693-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (-)-dimethyl-{2-[3-((R)-1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine
• 英文别名: dimethyl{2-[3-((R)-1-(pyridin-2-yl)ethyl)benzo[b]thiophen-2-yl]ethyl}amine；NBI-75043；dimethyl-{2-[3-((R)-1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine；Benzo(b)thiophene-2-ethanamine, N,N-dimethyl-3-((1R)-1-(2-pyridinyl)ethyl)-；N,N-dimethyl-2-[3-[(1R)-1-pyridin-2-ylethyl]-1-benzothiophen-2-yl]ethanamine
• CAS: 873693-47-1
• 化学式: C₁₉H₂₂N₂S
• 分子量: 310.463
• InChiKey: NANQRVOKMXDMNL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-dimethyl-{2-[3-((R)-1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine 在 1-氯乙基氯甲酸酯 、 N,N-二异丙基乙胺 、 盐酸 、 水 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl-{2-[3-((R)-1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine
  参考文献：
  名称：

  Sleep inducing compounds and methods relating thereto

  摘要：

  具有以下结构（I）的化合物，包括立体异构体、前药、以及其药用可接受的盐、酯和溶剂合物，其中R1、R2、R3a、R3b、L1、L2和n如本文所定义。这些化合物通常作为H1受体配体发挥作用，因此具有作为催眠药的用途。还披露了含有结构（I）化合物的药物组合物，以及与其使用相关的方法。

  公开号：

  US20060014797A1
• 作为产物：
  描述：

  dimethyl-{2-[3-(1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine 在 D-酒石酸 、 L-酒石酸 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以69%的产率得到(-)-dimethyl-{2-[3-((R)-1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine
  参考文献：
  名称：

  NBI-75043的化学开发。使用流动反应器规避分批限制的金属-卤素交换反应

  摘要：

  介绍了NBI-75043的发现路线和后续的放大路线。当发现传统的批处理化学方法限制了关键反应的规模时，设计并优化了流动反应器以提供另一种生产方法。

  DOI：

  10.1021/op800071m

文献信息

• Novel benzothiophene H1-antihistamines for the treatment of insomnia
  作者：Wilna J. Moree、Florence Jovic、Timothy Coon、Jinghua Yu、Bin-Feng Li、Fabio C. Tucci、Dragan Marinkovic、Raymond S. Gross、Siobhan Malany、Margaret J. Bradbury、Lisa M. Hernandez、Zhihong O’Brien、Jianyun Wen、Hua Wang、Samuel R.J. Hoare、Robert E. Petroski、Aida Sacaan、Ajay Madan、Paul D. Crowe、Graham Beaton

  DOI：10.1016/j.bmcl.2010.01.134

  日期：2010.4

  SAR of lead benzothiophene H-1-antihistamine 2 was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H-1-antihistamines with a range of projected half-lives in humans were identified. Compound 16d had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound. Compound 28b demonstrated lower predicted clearance in preclinical studies, and may represent a more suitable backup compound. (C) 2010 Elsevier Ltd. All rights reserved.
• Application of [BoPhoz Rh] catalysts in the asymmetric hydrogenation of a pyridyl benzothiophene alkene
  作者：Timothy Gross、Shine Chou、Alan Dyke、Beatriz Dominguez、Michelle Groarke、Jonathan Medlock、Michael Ouellette、Jayachandra P. Reddy、Andreas Seger、Scott Zook、Antonio Zanotti-Gerosa

  DOI：10.1016/j.tetlet.2011.12.038

  日期：2012.2

  The asymmetric hydrogenation of a pyridyl benzothiophene alkene has been successfully accomplished using [BoPhoz Rh] catalysts. By tailoring the steric properties of the BoPhoz ligand, the ee of the product could be increased from just 12% to 90%. This research further expands the substrate scope of the conventional class of functionalized alkenes amenable to catalytic asymmetric hydrogenation. (C) 2011 Elsevier Ltd. All rights reserved.
• Org. Process Res. Dev. 2008, 12, 929-939
  作者：

  DOI：——

  日期：——
• US7393865B2
  申请人：——

  公开号：US7393865B2

  公开（公告）日：2008-07-01
• [EN] SLEEP-INDUCING COMPOUNDS AND METHODS RELATED THERETO<br/>[FR] COMPOSES SOMNIFERES ET PROCEDES ASSOCIES
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2006019497A2

  公开（公告）日：2006-02-23

  Compounds having the following structure (I): including stereoisomers, prodrugs, and pharmaceutically acceptable salts, esters and solvates thereof, wherein R1, R2, R3a, R3b, L1, L2 and n are as defined herein. Such compounds generally function as H1 receptor ligands, and thus have utility as sleep inducing agents. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof, are also disclosed.