5-甲氧基吡啶-3-氨基甲酸叔丁酯 | 342603-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲氧基吡啶-3-氨基甲酸叔丁酯
• 中文别名: 3-BOC-氨基-5-甲氧基吡啶
• 英文名称: tert-butyl 5-methoxypyridin-3-ylcarbamate
• 英文别名: tert-butyl N-(5-methoxypyridin-3-yl)carbamate
• CAS: 342603-10-5
• 化学式: C₁₁H₁₆N₂O₃
• 分子量: 224.26
• InChiKey: FUSHCJZMKFNATD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-甲氧基吡啶-3-氨基甲酸叔丁酯 在 palladium diacetate 2,6-二甲基吡啶 、 过氧乙酸 、 4-二甲氨基吡啶 、 正丁基锂 、 水 、 sodium acetate 、 caesium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， -78.0~130.0 ℃ 、2.07 MPa 条件下， 反应 107.33h， 生成 methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate
  参考文献：
  名称：

  [EN] HIV INTEGRASE INHIBITORS
  [FR] INHIBITEURS DE L'INTÉGRASE VIH

  摘要：

  公式I的三环化合物是HIV整合酶的抑制剂和HIV复制的抑制剂：（I）其中G、T、R1、R2、R3A、R3B、R4A、R4B、R5A、R5B、R6A和R6B在此处定义。这些化合物可用于预防或治疗HIV感染以及预防、治疗或延缓艾滋病的发作或进展。这些化合物可作为化合物本身（或其水合物或溶剂化合物）或作为药学上可接受的盐形式来对抗HIV感染和艾滋病。这些化合物及其盐可作为药物组合物的成分，可选择性地与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用。

  公开号：

  WO2009154870A1
• 作为产物：
  描述：

  3,5-二溴吡啶 在 tris(dibenzylideneacetone)dipalladium (0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 caesium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 5-甲氧基吡啶-3-氨基甲酸叔丁酯
  参考文献：
  名称：

  Synthesis of a 5-alkoxypyrido[3,4-d]pyrimidin-4(3H)-one derivative via directed ortho-metallation of a pyridine analogue

  摘要：

  The synthetic strategy towards a 5-alkoxyprido[3,4-d]pyrimidin-4(3H)-one is described, utilizing palladium catalyzed amination of a bromopyridine, and subsequent directed ortho-metallation/carboxylation as the key steps. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.087

文献信息

• Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of MGLUR2 receptors
  申请人：Janssen Pharmaceutica NV

  公开号：US10005786B2

  公开（公告）日：2018-06-26

  The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives of Formula (I) as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 (“mGluR2”). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved.

  本发明涉及式 (I) 的新型 6,7-二氢吡唑并[1,5-a]吡嗪-4(5H)-酮衍生物 作为代谢型谷氨酸受体亚型 2（"mGluR2"）的负异位调节剂（NAMs）。本发明还涉及包含此类化合物的药物组合物、制备此类化合物和组合物的工艺，以及使用此类化合物和组合物预防或治疗涉及代谢型受体 mGluR2 亚型的疾病。
• Process Development of a Novel Azetidinyl Ketolide Antibiotic
  作者：Bryan Li、Thomas V. Magee、Richard A. Buzon、Daniel W. Widlicka、Dave R. Bill、Thomas Brandt、Xiaoping Cao、Michael Coutant、Haijian Dou、Karl Granskog、Mark E. Flanagan、Cheryl M. Hayward、Bin Li、Fengwei Liu、Wei Liu、Thuy-Trinh Nguyen、Jeffrey W. Raggon、Peter Rose、Joseph Rainville、Usa Datta Reilly、Yue Shen、Jianmin Sun、Glenn E. Wilcox

  DOI：10.1021/op300064b

  日期：2012.5.18

  Process development and the multikilogram synthesis of a novel azetidinyl ketolide antibiotic is described. Starting with clarithromycin, the eight-step synthesis features several telescoped operations and direct isolations, which results in a significant improvement in throughput and a major reduction in solvent usage and waste stream volume over the first scale-up campaign. Particular highlights of this effort include the development of an efficient synthesis of 3-hydroxy-1,5-naphthyridine-4-carbaldehyde via a Skraup process and engineering a robust final API synthesis. We also discovered a crystalline monotosylate salt that addressed significant formulation and degradation issues experienced when using the noncrystalline freebase.
• A Multifunctional Reagent Designed for the Site-Selective Amination of Pyridines
  作者：Patrick S. Fier、Suhong Kim、Ryan D. Cohen

  DOI：10.1021/jacs.0c03537

  日期：2020.5.13

  We report the development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines with exquisite site selectivity and chemoselectivity. The novel reagent was prepared on 200-g scale in a single step, reacts in the title reaction under mild conditions without precautions toward air or moisture, and is tolerant of nearly all common functionality. Experimental and in situ spectroscopic monitoring techniques provide detailed insights and unexpected findings for the unique reaction mechanism.
• Discovery of Azetidinyl Ketolides for the Treatment of Susceptible and Multidrug Resistant Community-Acquired Respiratory Tract Infections
  作者：Thomas V. Magee、Sharon L. Ripp、Bryan Li、Richard A. Buzon、Lou Chupak、Thomas J. Dougherty、Steven M. Finegan、Dennis Girard、Anne E. Hagen、Michael J. Falcone、Kathleen A. Farley、Karl Granskog、Joel R. Hardink、Michael D. Huband、Barbara J. Kamicker、Takushi Kaneko、Michael J. Knickerbocker、Jennifer L. Liras、Andrea Marra、Ivy Medina、Thuy-Trinh Nguyen、Mark C. Noe、R. Scott Obach、John P. O’Donnell、Joseph B. Penzien、Usa Datta Reilly、John R. Schafer、Yue Shen、Gregory G. Stone、Timothy J. Strelevitz、Jianmin Sun、Amelia Tait-Kamradt、Alfin D. N. Vaz、David A. Whipple、Daniel W. Widlicka、Donn G. Wishka、Joanna P. Wolkowski、Mark E. Flanagan

  DOI：10.1021/jm900729s

  日期：2009.12.10

  Respiratory tract bacterial strains are becoming increasingly resistant to currently marketed macrolide antibiotics. The current alternative telithromycin (1) from the newer ketolide class of macrolides addresses resistance but is hampered by serious safety concerns, hepatotoxicity in particular. We have discovered a novel series of azetidinyl ketolides that focus on mitigation of hepatotoxicity by minimizing hepatic turnover and time-dependent inactivation of CYP3A isoforms in the liver without compromising the potency and efficacy of 1.
• GAMMA-HYDROXY-2-(FLUOROALKYLAMINOCARBONYL)-1-PIPERAZINEPENTANAMIDES AS HIV PROTEASE INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1242426B1

  公开（公告）日：2007-10-31