1-(2-chloro-pyridin-3-yl)-1-(4-methoxy-benzyl)urea | 906532-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-chloro-pyridin-3-yl)-1-(4-methoxy-benzyl)urea
• 英文别名: 1-(2-Chloropyridin-3-yl)-1-[(4-methoxyphenyl)methyl]urea；1-(2-chloropyridin-3-yl)-1-[(4-methoxyphenyl)methyl]urea
• CAS: 906532-78-3
• 化学式: C₁₄H₁₄ClN₃O₂
• 分子量: 291.737
• InChiKey: UZMUPHVXVYRHSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-pyridin-3-yl)-1-(4-methoxy-benzyl)urea 在 palladium diacetate 、 1,4-双(二苯基膦)丁烷 水 、 碳酸氢钠 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以95%的产率得到1-(4-methoxy-benzyl)-1,3-dihydroimidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j
• 作为产物：
  描述：

  (2-chloropyridin-3-yl)-(4-methoxybenzyl)amine 在 水 作用下， 以 四氢呋喃 、 醋酸异丙酯 为溶剂， 反应 1.17h， 生成 1-(2-chloro-pyridin-3-yl)-1-(4-methoxy-benzyl)urea
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j

文献信息

• Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization
  作者：Mark McLaughlin、Michael Palucki、Ian W. Davies

  DOI：10.1021/ol061233j

  日期：2006.7.1

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.