2-methyl-N-(pyridin-2-yl)benzamide | 35498-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-N-(pyridin-2-yl)benzamide
• 英文别名: 2-Methyl-N-pyridin-2-yl-benzamide；2-methyl-N-pyridin-2-ylbenzamide
• CAS: 35498-29-4
• 化学式: C₁₃H₁₂N₂O
• mdl: MFCD00543213
• 分子量: 212.251
• InChiKey: MRKIJNKNOOCNBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-N-(pyridin-2-yl)benzamide 、 碘甲烷 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 以16%的产率得到N,2-dimethyl-N-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  Pyridyl Benzamides as a Novel Class of Potent Inhibitors for the Kinetoplastid Trypanosoma brucei

  摘要：

  A whole-organism screen of approximately 87000 compounds against Trypanosoma brucei brucei identified a number of promising compounds for medicinal chemistry optimization. One of these classes of compounds we termed the pyridyl benzamides. While the initial hit had an IC50 of 12 μM, it was small enough to be attractive for further optimization, and we utilized three parallel approaches to develop the structure-activity relationships. We determined that the physicochemical properties for this class are generally favorable with particular positions identified that appear to block metabolism when substituted and others that modulate solubility. Our most active compound is 79, which has an IC50 of 0.045 μM against the human pathogenic strain Trypanosoma brucei rhodesiense and is more than 4000 times less active against the mammalian L6 cell line.

  DOI：

  10.1021/jm500191u
• 作为产物：
  描述：

  N-cyclohexyl-2-(o-tolyl)imidazolo[1,2-a]pyridin-3-amine 在 potassium tert-butylate 、 copper diacetate 作用下， 以 邻二甲苯 为溶剂， 反应 8.0h， 以81%的产率得到2-methyl-N-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  一种N-杂环酰胺衍生物的合成方法

  摘要：

  本发明公开了一种N‑杂环酰胺衍生物的合成方法，反应通式如下。即：以咪唑并杂环胺类化合物I为原料，在催化剂的作用下，在碱性条件下于有机溶剂中和80～200℃的条件下与空气或氧气发生反应开环，同时插入氧原子，生成如反应通式所示的N‑杂环酰胺衍生物II。本方法具有操作简单、收率高、底物普适性广等特点。

  公开号：

  CN109053558B

文献信息

• Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHept^Cl)Pd Promoted by Trialkylboranes or B(C₆F₅)₃
  作者：Sepideh Sharif、Jonathan Day、Howard N. Hunter、Yu Lu、David Mitchell、Michael J. Rodriguez、Michael G. Organ

  DOI：10.1021/jacs.7b09488

  日期：2017.12.27

  the coupling of amide nucleophiles to a wide variety of oxidative addition partners using Pd-NHC catalysts. Through a combination of NMR spectroscopy and control studies with and without oxygen and radical scavengers, we propose that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive

  硼衍生的路易斯酸已被证明可以使用 Pd-NHC 催化剂有效地促进酰胺亲核试剂与各种氧化加成伙伴的偶联。通过结合 NMR 光谱和有和没有氧和自由基清除剂的对照研究，我们建议在基本反应条件下形成硼酰亚胺，这有助于氮与 Pd(II) 的配位，这是限速的，并直接提供中间体用于还原消除。
• Metal-Free Synthesis of <i>N</i>-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)–C(Alkyl) Bond in Water
  作者：Yanpeng Liu、Honghao Sun、Zhangjian Huang、Cong Ma、Aijun Lin、Hequan Yao、Jinyi Xu、Shengtao Xu

  DOI：10.1021/acs.joc.8b01956

  日期：2018.12.7

  N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C–C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate

  已经开发了TBHP / TBAI介导的通过直接氧化CC键从酮和2-氨基吡啶合成水中N-（吡啶-2-基）酰胺的方法。一系列酮，包括被各种长链烷基取代的更具挑战性的惰性芳族酮，被选择性地转化为N-（吡啶-2-基）酰胺。此外，该方案可以应用于芳基烷基甲醇，以中等至良好的产率得到相应的酰胺。
• Direct Transformation of Alkylarenes into <i>N</i> ‐(Pyridine‐2‐yl)amides by C(sp ³ )–C(sp ³ ) Bond Cleavage
  作者：Haipin Zhou、Yanpeng Liu、Haidong Xia、Jinyi Xu、Tingfang Wang、Shengtao Xu

  DOI：10.1002/ejoc.202001137

  日期：2020.11.8

  A mild and green methodology for the construction of N‐(pyridine‐2‐yl)amides from alkylarenes and 2‐aminopyridine in one step was developed. Various alkylarenes were directly transformed into the corresponding N‐(pyridine‐2‐yl)amides through tandem C(sp3)–H bond activation/oxidative cyclization/C–C bond cleavage.

  开发了一种温和且绿色的方法，可一步一步从烷基芳烃和2-氨基吡啶构建N-（吡啶-2-基）酰胺。通过串联C（sp 3）-H键活化/氧化环化/ CC键断裂，各种烷基芳烃直接转化为相应的N-（吡啶-2-基）酰胺。
• Copper(I)-catalysed aerobic oxidative selective cleavage of C C bond with DMAP: Facile access to N-substituted benzamides
  作者：Haojie Ma、Guoqiang Lu、Bo Han、Guosheng Huang、Yuqi Zhang、Ji-Jiang Wang

  DOI：10.1016/j.tetlet.2021.153199

  日期：2021.7

  cleavage of C(CO)–C(alkyl) bond to generate N-substituted benzamides has been developed in the presence of copper(I) chloride. The usage of inexpensive copper catalyst, broad substrate scope, mild conditions make this protocol very practical. More importantly, this reaction provides an alternative approach for the construction of useful N-substituted benzamides.

  在氯化铜 (I) 存在下，开发了一种碱/DMAP 系统，用于有效氧化裂解 C(CO)–C(烷基) 键以生成N取代的苯甲酰胺。使用廉价的铜催化剂、广泛的底物范围、温和的条件使该协议非常实用。更重要的是，该反应为构建有用的N-取代苯甲酰胺提供了一种替代方法。
• Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C–C and C–N bonds
  作者：Kelu Yan、Daoshan Yang、Wei Wei、Guoqing Li、Mingyang Sun、Qingyun Zhang、Laijin Tian、Hua Wang

  DOI：10.1039/c5ra17740e

  日期：——

  A highly regioselective TBHP-mediated ring opening of imidazopyridinesviacleavage of C–C and C–N bonds has been realized for the first time to afford usefulN-(pyridin-2-yl)benzamides under mild conditions.

  通过首次实现高度区域选择性的TBHP介导的咪唑吡啶环开启，通过断裂C-C和C-N键，在温和条件下得到有用的N-(吡啒啒-2-基)苯甲酰胺。