N-pyrid-2-yl-N-(6-methylpyrid-2-yl)amine | 342653-84-3

• 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: N-pyrid-2-yl-N-(6-methylpyrid-2-yl)amine
• 英文别名: 6-methyl-N-pyridin-2-ylpyridin-2-amine
• CAS: 342653-84-3
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: ZGIHPZDQDJRCHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-norbornene-endo-2-carbonyl chloride 、 N-pyrid-2-yl-N-(6-methylpyrid-2-yl)amine 以 二氯甲烷 为溶剂， 反应 18.0h， 以38%的产率得到N-pyrid-2-yl-N-(6-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide
  参考文献：
  名称：

  N-Acyl-N,N-dipyridyl and N-acyl-N-pyridyl-N-quinoyl amine based palladium complexes. Synthesis, X-ray structures, heterogenization and use in Heck couplings

  摘要：

  A series of homogeneous and heterogeneous palladium(II)-catalysts and their use in Heck-couplings is described. Starting from four different amines, N-pyrid-2-yl-N-(3-methylpyrid-2-yl) amine (1), N-pyrid-2-yl-N-(6-methylpyrid-2-yl) amine (2), N-(6-methylpyrid-2-yl)-N-(4-methylquinolin-2-yl)amine (3) and N-bis (6-methylpyrid-2-yl) amine (4), the corresponding acetyl- and norbornene derivatives, N-pyrid-2-yl-N-(3-methylpyrid-2-yl) acetamide (5), N-pyrid-2-yl-N-(6-methylpyrid-2-yl) acetamide (6), N-(6-methylpyrid-2-yl) -N-(4-methylquinolin-2-yl) acetamide (7), N-bis (6-methylpyrid-2-yl) acetamide (8) and N-pyrid-2-yl-N-(3-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide (9), N-pyrid-2-yl-N-(6-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide (10) and N-(6-methylpyrid-2-yl) -N-(4-methylquinolin-2-yl)-endo-norborn-2-ene-5-carbamide (11), respectively, have been prepared. The acetyl derivatives 5-8 have been used for the preparation of the homogeneous Heck catalysts N-acetyl-N-pyrid-2-yl-N-(3-methylpyrid-2-yl)amine palladium dichloride (13), N-acetyl-N-pyrid-2-yl-N-(6-methylpyrid-2-yl) amine palladium dichloride (14), N-acetyl-N-(6-methylpyrid-2-yl)-N- (4-methylquinolin-2-yl) amine palladium dichloride (15) and N-acetyl-N-bis(6-methylpyrid-2-yl)amine palladium dichloride (16). X-ray data were obtained for compounds 9, 11, 13 and 14. Polymer supports 17-19 were prepared via ring-opening metathesis copolymerization of the norbornene derivatives 9-11 with 1,4,4a,5,8,8a-hexahydro-1,4,5,8-exo-endo-dimethano-naphthalene (HDMN-6) and subsequently loaded with palladium(II) chloride. Both the homogeneous catalysts 13-16 and the heterogeneous catalysts are active in the vinylation of aryl iodides and aryl bromides with turn-over numbers (TONs) of up to 220 000. Comparably low yields (= 34%) and TONs (= 2100) are achieved in the tetrabutylammonium bromide- (TBAB-) assisted vinylation of aryl chlorides as well as in the amination of aryl bromides. Structural data of compounds 9, 11, 13 and 14 were compared with those of the parent systems, N-acetyldipyridylamine palladiumdichloride (20) and the poly(N,N-dipyrid-2-yl-endo-norborn-2-ene-5-carbamide)based resin (21), respectively. Thus, methyl-substitution leads to a significant perturbation of the almost perfect square planar coordination of Pd found in 20 resulting in lowered stabilities of the corresponding Pd-complexes 13-16 and consequently lowered coupling yields compared to 20 and 21. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00783-x
• 作为产物：
  描述：

  2-溴吡啶 、 2-氨基-6-甲基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 二苯基丙基膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以96%的产率得到N-pyrid-2-yl-N-(6-methylpyrid-2-yl)amine
  参考文献：
  名称：

  N-Acyl-N,N-dipyridyl and N-acyl-N-pyridyl-N-quinoyl amine based palladium complexes. Synthesis, X-ray structures, heterogenization and use in Heck couplings

  摘要：

  A series of homogeneous and heterogeneous palladium(II)-catalysts and their use in Heck-couplings is described. Starting from four different amines, N-pyrid-2-yl-N-(3-methylpyrid-2-yl) amine (1), N-pyrid-2-yl-N-(6-methylpyrid-2-yl) amine (2), N-(6-methylpyrid-2-yl)-N-(4-methylquinolin-2-yl)amine (3) and N-bis (6-methylpyrid-2-yl) amine (4), the corresponding acetyl- and norbornene derivatives, N-pyrid-2-yl-N-(3-methylpyrid-2-yl) acetamide (5), N-pyrid-2-yl-N-(6-methylpyrid-2-yl) acetamide (6), N-(6-methylpyrid-2-yl) -N-(4-methylquinolin-2-yl) acetamide (7), N-bis (6-methylpyrid-2-yl) acetamide (8) and N-pyrid-2-yl-N-(3-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide (9), N-pyrid-2-yl-N-(6-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide (10) and N-(6-methylpyrid-2-yl) -N-(4-methylquinolin-2-yl)-endo-norborn-2-ene-5-carbamide (11), respectively, have been prepared. The acetyl derivatives 5-8 have been used for the preparation of the homogeneous Heck catalysts N-acetyl-N-pyrid-2-yl-N-(3-methylpyrid-2-yl)amine palladium dichloride (13), N-acetyl-N-pyrid-2-yl-N-(6-methylpyrid-2-yl) amine palladium dichloride (14), N-acetyl-N-(6-methylpyrid-2-yl)-N- (4-methylquinolin-2-yl) amine palladium dichloride (15) and N-acetyl-N-bis(6-methylpyrid-2-yl)amine palladium dichloride (16). X-ray data were obtained for compounds 9, 11, 13 and 14. Polymer supports 17-19 were prepared via ring-opening metathesis copolymerization of the norbornene derivatives 9-11 with 1,4,4a,5,8,8a-hexahydro-1,4,5,8-exo-endo-dimethano-naphthalene (HDMN-6) and subsequently loaded with palladium(II) chloride. Both the homogeneous catalysts 13-16 and the heterogeneous catalysts are active in the vinylation of aryl iodides and aryl bromides with turn-over numbers (TONs) of up to 220 000. Comparably low yields (= 34%) and TONs (= 2100) are achieved in the tetrabutylammonium bromide- (TBAB-) assisted vinylation of aryl chlorides as well as in the amination of aryl bromides. Structural data of compounds 9, 11, 13 and 14 were compared with those of the parent systems, N-acetyldipyridylamine palladiumdichloride (20) and the poly(N,N-dipyrid-2-yl-endo-norborn-2-ene-5-carbamide)based resin (21), respectively. Thus, methyl-substitution leads to a significant perturbation of the almost perfect square planar coordination of Pd found in 20 resulting in lowered stabilities of the corresponding Pd-complexes 13-16 and consequently lowered coupling yields compared to 20 and 21. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00783-x

文献信息

• [EN] BIPYRIDYL AMINES AND ETHERS AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5<br/>[FR] AMINES ET ETHERS DE BIPYRIDYLE UTILISES COMME MODULATEURS DU RECEPTEUR 5 METABOTROPIQUE AU GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2005021529A1

  公开（公告）日：2005-03-10

  The present invention is directed to novel bipyridyl amine and ether compounds such as those of Formula (I): (I) (where R?1#191, R?2#191, R?3#191, X and Y are as defined herein) which are mGluR5 modulators useful in the treatment or prevention of diseases and conditions in which mGluR5 is involved, including but not limited to psychiatric and mood disorders such as schizophrenia, anxiety, depression, bipolar disorders, and panic, as well as in the treatment of pain, Parkinson’s disease, cognitive dysfunction, epilepsy, circadian rhythm and sleep disorders, such as shift-work induced sleep disorder and jet-lag, drug addiction, drug abuse, drug withdrawal, obesity and other diseases. The invention is also directed to pharmaceutical compositions comprising these compounds. This invention further provides a method of treatment of these disorders and conditions by the administration of an effective amount of these novel bipyridyl amine and/or ether compounds and/or compositions containing these compounds.

  本发明涉及一种新型的双吡啶基胺和醚化合物，例如式(I)中的化合物：（I）（其中R?1#191，R?2#191，R?3#191，X和Y的定义如本文所述），这些化合物是mGluR5调节剂，可用于治疗或预防涉及mGluR5的疾病和症状，包括但不限于精神和情绪障碍，如精神分裂症、焦虑、抑郁症、双相情感障碍和恐慌，以及用于疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律和睡眠障碍，如倒班工作引起的睡眠障碍和时差反应，药物成瘾、药物滥用、戒断综合征、肥胖症和其他疾病的治疗。本发明还涉及包含这些化合物的药物组合物。本发明还提供了一种通过给予这些新型双吡啶基胺和/或醚化合物和/或含有这些化合物的组合物的有效量来治疗这些障碍和症状的方法。
• LIGAND EXCHANGE THERMOCHROMIC SYSTEMS AND HIGH E LIGANDS FOR SAME
  申请人：Byker J. Harlan

  公开号：US20080105851A1

  公开（公告）日：2008-05-08

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. In accordance with certain aspects of the present invention, a thermochromic system is disclosed comprising a transition metal ion and a ligand wherein the ligand comprises a nitrogen-containing five or six membered heterocyclic compound that coordinates through the nitrogen atom to the transition metal ion in a HεMLC formed between the transition metal ion and the ligand. In accordance with other aspects of the present invention, thermochromic systems are disclosed comprising a transition metal ion with particularly useful ligands, such as phosphine compounds, tridentate ligands that coordinate through three nitrogen atoms, bidentate ligands, or ortho hindered pyridine monodentate ligands.

  本文描述了具有热致变色性质的配体交换（LETC）系统，当系统的温度可逆变化时，电磁辐射吸收率也可逆变化。所述的LETC系统包括一个或多个过渡金属离子，其经历热诱导的配位或配位环境的变化，从而使系统随着温度变化而改变吸收电磁辐射的能力。根据本发明的某些方面，公开了包括过渡金属离子和配体的热致变色系统，其中配体包括通过氮原子与过渡金属离子形成的HεMLC（配体与过渡金属离子之间的配位键）的含氮五元或六元杂环化合物。根据本发明的其他方面，公开了包括具有特别有用的配体的过渡金属离子的热致变色系统，例如膦化合物、通过三个氮原子配位的三齿配体、双齿配体或邻位受阻的吡啶单齿配体。
• LIGAND EXCHANGE THERMOCHROMIC SYSTEMS CONTAINING EXCHANGE METALS
  申请人：Byker J. Harlan

  公开号：US20080106781A1

  公开（公告）日：2008-05-08

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. In accordance with one aspect of the present invention, a thermochromic system is disclosed comprising a first metal ion and a second metal ion and at least one ligand that complexes with the first metal ion to form a LεMLC and complexes with the second metal ion to form a HεMLC wherein an increase in temperature of the system results in a reversible net increase in its ability to absorb light energy in the 400 nm to 1400 nm range due to the ligand transferring from the first metal ion to the second metal ion.

  本文介绍了一种具有热致变色特性的配体交换系统，当系统的温度可逆变化时，其吸收电磁辐射的能力也可逆变化。所述的LETC系统包括一个或多个过渡金属离子，其在过渡金属离子周围的络合或配位发生热诱导变化，从而使系统随着温度变化而改变吸收电磁辐射的能力。根据本发明的一个方面，公开了一种热致变色系统，包括第一金属离子和第二金属离子以及至少一个配体，该配体与第一金属离子形成LεMLC配合物，并与第二金属离子形成HεMLC配合物，系统温度的升高导致可逆的净吸收光能力增加，范围为400纳米至1400纳米，这是由于配体从第一金属离子转移到第二金属离子造成的。
• LIGAND EXCHANGE THERMOCHROMIC, (LETC), SYSTEMS
  申请人：Byker J. Harlan

  公开号：US20080100902A1

  公开（公告）日：2008-05-01

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes.

  本文介绍了一种热致变色（LETC）系统的配体交换方法，该系统在温度可逆变化时显示出电磁辐射吸收的可逆变化。所述LETC系统包括一个或多个过渡金属离子，其在过渡金属离子周围的配位或络合性质发生热诱导变化，从而使系统在温度变化时改变吸收电磁辐射的能力。
• Bipyridyl amines and ethers as modulators of metabotropic glutamate receptor-5
  申请人：Kamenecka M. Theodore

  公开号：US20070027321A1

  公开（公告）日：2007-02-01

  The present invention is directed to novel bipyridyl amine and ether compounds such as those of Formula (I): (I) (where R?1#191, R?2#191, R?3#191, X and Y are as defined herein) which are mGluR5 modulators useful in the treatment or prevention of diseases and conditions in which mGluR5 is involved, including but not limited to psychiatric and mood disorders such as schizophrenia, anxiety, depression, bipolar disorders, and panic, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm and sleep disorders, such as shift-work induced sleep disorder and jet-lag, drug addiction, drug abuse, drug withdrawal, obesity and other diseases. The invention is also directed to pharmaceutical compositions comprising these compounds. This invention further provides a method of treatment of these disorders and conditions by the administration of an effective amount of these novel bipyridyl amine and/or ether compounds and/or compositions containing these compounds.

  本发明涉及新型的联吡啶胺和醚化合物，例如公式(I)中的化合物：(I) (其中R?1#191，R?2#191，R?3#191，X和Y如本文所定义)，这些化合物是mGluR5调节剂，可用于治疗或预防涉及mGluR5的疾病和病况，包括但不限于精神和情绪障碍，如精神分裂症、焦虑、抑郁、双相障碍和惊恐，以及治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律和睡眠障碍，如倒班工作引起的睡眠障碍和时差反应、药物成瘾、药物滥用、戒断综合征、肥胖症和其他疾病。本发明还涉及包含这些化合物的药物组合物。本发明还提供了通过给予这些新型联吡啶胺和/或醚化合物和/或含有这些化合物的组合物的有效量来治疗这些障碍和病况的方法。