1-benzyl-N-methyl-1H-benzo[d]imidazol-2-amine | 43181-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-benzyl-N-methyl-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-benzyl-N-methyl-1H-benzo[d]imidazole-2-amine；1-Benzyl-N-methyl-1H-benzimidazol-2-amine；1-benzyl-N-methylbenzimidazol-2-amine
• CAS: 43181-77-7
• 化学式: C₁₅H₁₅N₃
• 分子量: 237.304
• InChiKey: QTIDUMRDGLRSIV-UHFFFAOYSA-N

物化性质

• 沸点：
  421.9±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 1-benzyl-N-methyl-1H-benzo[d]imidazol-2-amine 在 sodium hydroxide 、 水 作用下， 以89%的产率得到(1-benzyl-2-methylimino-2,3-dihydro-1H-benzimidazol-3-yl)acetic acid ethyl ester
  参考文献：
  名称：

  Da Settimo; Marini; Bianucci, Il Farmaco, 1994, vol. 49, # 12, p. 829 - 834

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯并咪唑 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 13.5h， 生成 1-benzyl-N-methyl-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903

  摘要：

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.

  DOI：

  10.1016/j.bmcl.2018.12.007

文献信息

• Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate
  作者：Peng Liu、Jiazhi Yang、Yao Ai、Shushu Hao、Xiaozhong Chen、Feng Li

  DOI：10.1016/j.jcat.2021.02.030

  日期：2021.4

  An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete

  铱络合物Cp * Ir @ CTF是通过将[Cp * IrCl 2 ] 2配位固定在功能化的共价三嗪骨架（CTF）上合成的，它是一种通用的高效N-甲基化催化剂在碳酸盐的存在下，将胺与甲醇反应。在环境友好的条件下，以高收率获得了各种理想的产品，具有完全的选择性和对官能团的友好性。此外，合成的催化剂可以通过简单的过滤进行再循环，而在第六次循环后没有明显的催化活性损失。值得注意的是，这项研究显示了共价三嗪骨架负载的过渡金属催化剂在氢自动转移过程中的潜力。
• General and efficient method for direct N-monomethylation of aromatic primary amines with methanol
  作者：Feng Li、Jianjiang Xie、Haixia Shan、Chunlou Sun、Lin Chen

  DOI：10.1039/c2ra21487c

  日期：——

  The direct N-monomethylation of aromatic primary amines, including arylamines, arylsulfonamides and amino-azoles, using methanol as a methylating agent has been accomplished in the presence of a [Cp*IrCl2]2/NaOH system. From both synthetic and environmental points of view, the reaction is highly attractive because of low catalyst loading, broad substrate scope and excellent selectivities.

  芳族伯胺的直接N-单甲基化反应，包括芳胺，芳基磺酰胺和氨基唑甲醇在[Cp * IrCl 2 ] 2 / NaOH体系的存在下已经完成了甲基化。从合成和环境的角度来看，由于催化剂用量低，底物范围宽和选择性好，该反应具有很高的吸引力。
• <i>N</i>-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal–Ligand Bifunctional Ruthenium Catalyst [(<i>p</i>-cymene)Ru(2,2′-bpyO)(H₂O)]
  作者：Peng Liu、Nguyen Thanh Tung、Xiangchao Xu、Jiazhi Yang、Feng Li

  DOI：10.1021/acs.joc.0c02685

  日期：2021.2.5
• <i>N</i>-Methylation of Amines with Methanol Catalyzed by a Cp*Ir Complex Bearing a Functional 2,2′-Bibenzimidazole Ligand
  作者：Ran Liang、Shun Li、Rongzhou Wang、Lei Lu、Feng Li

  DOI：10.1021/acs.orglett.7b02723

  日期：2017.11.3

  A new type of Cp*Ir complex bearing a functional 2,2'-bibenzimidazole ligand was designed, synthesized, and found to be a highly effective and general catalyst for the N-methylation of a variety of amines with methanol in the presence of a weak base (0.3 equiv of Cs2CO3).
• Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903
  作者：Swagat H. Sharma、Juan Lorenzo Pablo、Monica Suarez Montesinos、Anna Greka、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2018.12.007

  日期：2019.1

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.