N-cyclohexyl-4-formyl-2-methoxy-N-propan-2-ylbenzamide

• 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: N-cyclohexyl-4-formyl-2-methoxy-N-propan-2-ylbenzamide
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: KXMMILWAZOOWAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-氨基-2-吡啶基)甲酰胺 、 N-cyclohexyl-4-formyl-2-methoxy-N-propan-2-ylbenzamide 在 吡啶硼烷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 以74%的产率得到N-Cyclohexyl-4-(1H-imidazo<4,5-b>pyridin-1-ylmethyl)-2-methoxy-N-(1-methylethyl)benzamide
  参考文献：
  名称：

  Facile, Regioselective Syntheses of N-Alkylated 2,3-Diaminopyridines and Imidazo[4,5-b]pyridines

  摘要：

  Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to give predominantly the N-3 alkylated products, which have been used for the regioselective synthesis of N-1 substituted imidazo[4,5-b]pyridines. Investigations using 2-formamido-3-aminopyridine (13), synthesized in two steps from 2-amino-3-nitropyridine, show it to be a versatile intermediate for the regioselective synthesis of either N-1 or N-3 substituted imidazo[4,5-b]pyridines, depending upon the conditions employed. The reductive amination of aldehydes with 13 using borane-pyridine in acetic acid affords the N-1 substituted imidazo[4,5-b]pyridines in one step, whereas reaction of 13 with alkyl halides in the presence of a suitable base (e.g., cesium carbonate) yields the N-3 substituted imidazo[4,5-b]pyridines. The generality of this synthetic methodology is noted.

  DOI：

  10.1021/jo00109a029

文献信息

• Facile, Regioselective Syntheses of N-Alkylated 2,3-Diaminopyridines and Imidazo[4,5-b]pyridines
  作者：Ish K. Khanna、Richard M. Weier、Kirk T. Lentz、Lydia Swenton、David C. Lankin

  DOI：10.1021/jo00109a029

  日期：1995.2

  Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to give predominantly the N-3 alkylated products, which have been used for the regioselective synthesis of N-1 substituted imidazo[4,5-b]pyridines. Investigations using 2-formamido-3-aminopyridine (13), synthesized in two steps from 2-amino-3-nitropyridine, show it to be a versatile intermediate for the regioselective synthesis of either N-1 or N-3 substituted imidazo[4,5-b]pyridines, depending upon the conditions employed. The reductive amination of aldehydes with 13 using borane-pyridine in acetic acid affords the N-1 substituted imidazo[4,5-b]pyridines in one step, whereas reaction of 13 with alkyl halides in the presence of a suitable base (e.g., cesium carbonate) yields the N-3 substituted imidazo[4,5-b]pyridines. The generality of this synthetic methodology is noted.