1-benzyl-1-(2-chloro-pyridin-3-yl)urea | 906532-74-9

• 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: 1-benzyl-1-(2-chloro-pyridin-3-yl)urea
• 英文别名: 1-Benzyl-1-(2-chloropyridin-3-yl)urea；1-benzyl-1-(2-chloropyridin-3-yl)urea
• CAS: 906532-74-9
• 化学式: C₁₃H₁₂ClN₃O
• 分子量: 261.711
• InChiKey: WPUKHINIXBJTRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-1-(2-chloro-pyridin-3-yl)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1,3-Dihydro-1-(phenylmethyl)-2H-imidazo<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：

  3-氨基-2-氯吡啶 在 水 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 醋酸异丙酯 为溶剂， 反应 1.34h， 生成 1-benzyl-1-(2-chloro-pyridin-3-yl)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.