6-chloro-N2-isobutylpyridine-2,3-diamine | 1186395-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-chloro-N2-isobutylpyridine-2,3-diamine
• 英文别名: 6-Chloro-N2-isobutylpyridine-2,3-diamine；6-chloro-2-N-(2-methylpropyl)pyridine-2,3-diamine
• CAS: 1186395-64-1
• 化学式: C₉H₁₄ClN₃
• 分子量: 199.683
• InChiKey: SCBGVYQKYQKVJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-N2-isobutylpyridine-2,3-diamine 在 盐酸 、 三氯氧磷 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 5.5h， 生成 5-chloro-3-isobutyl-3H-imidazo[4,5-b]pyridin-2-amine
  参考文献：
  名称：

  Preparation of 2-Aminopyridoimidazoles and 2-Aminobenzimidazoles via Phosphorus Oxychloride-Mediated Cyclization of Aminoureas

  摘要：

  The novel preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via the cyclization of (2-aminopyridin-3-yl)urea and (2-aminophenyl)urea substrates in the presence of phosphorus oxychloride is described. This methodology is demonstrated for a range of urea substrates with aminoimidazole products obtained in good yields and with excellent levels of purity.

  DOI：

  10.1021/jo500360k
• 作为产物：
  描述：

  6-chloro-N-isobutyl-3-nitropyridin-2-amine 在 platinum on carbon 、 氢气 、 次磷酸 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以97.6%的产率得到6-chloro-N2-isobutylpyridine-2,3-diamine
  参考文献：
  名称：

  Preparation of 2-Aminopyridoimidazoles and 2-Aminobenzimidazoles via Phosphorus Oxychloride-Mediated Cyclization of Aminoureas

  摘要：

  The novel preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via the cyclization of (2-aminopyridin-3-yl)urea and (2-aminophenyl)urea substrates in the presence of phosphorus oxychloride is described. This methodology is demonstrated for a range of urea substrates with aminoimidazole products obtained in good yields and with excellent levels of purity.

  DOI：

  10.1021/jo500360k

文献信息

• Identification, synthesis and SAR of amino substituted pyrido[3,2b]pyrazinones as potent and selective PDE5 inhibitors
  作者：Dafydd R. Owen、John K. Walker、E. Jon Jacobsen、John N. Freskos、Robert O. Hughes、David L. Brown、Andrew S. Bell、David G. Brown、Christopher Phillips、Brent V. Mischke、John M. Molyneaux、Yvette M. Fobian、Steve E. Heasley、Joseph B. Moon、William C. Stallings、D. Joseph Rogier、David N.A. Fox、Michael J. Palmer、Tracy Ringer、Margarita Rodriquez-Lens、Jerry W. Cubbage、Radhika M. Blevis-Bal、Alan G. Benson、Brad A. Acker、Todd M. Maddux、Michael B. Tollefson、Brian R. Bond、Alan MacInnes、Yung Yu

  DOI：10.1016/j.bmcl.2009.06.012

  日期：2009.8

  A new class of potent and selective PDE5 inhibitors is disclosed. Guided by X-ray crystallographic data, optimization of an HTS lead led to the discovery of a series of 2-aryl, (N8)-alkyl substituted-6-aminosubstituted pyrido[3,2b]pyrazinones which show potent inhibition of the PDE5 enzyme. Synthetic details and some structure-activity relationships are also presented. (C) 2009 Elsevier Ltd. All rights reserved.
• Preparation of 2-Aminopyridoimidazoles and 2-Aminobenzimidazoles via Phosphorus Oxychloride-Mediated Cyclization of Aminoureas
  作者：Rebecca E. Deasy、Catherine N. Slattery、Anita R. Maguire、Douglas P. Kjell、Mai Khanh N. Hawk、Jung Min Joo、Rui Lin Gu、Humphrey Moynihan

  DOI：10.1021/jo500360k

  日期：2014.4.18

  The novel preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via the cyclization of (2-aminopyridin-3-yl)urea and (2-aminophenyl)urea substrates in the presence of phosphorus oxychloride is described. This methodology is demonstrated for a range of urea substrates with aminoimidazole products obtained in good yields and with excellent levels of purity.