4-((6-chloro-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)morpholine | 1422006-68-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((6-chloro-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)morpholine
• 英文别名: Imidazo[1,2-b]pyridazine, 6-chloro-2-methyl-8-(4-morpholinylmethyl)-；4-[(6-chloro-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl]morpholine
• CAS: 1422006-68-5
• 化学式: C₁₂H₁₅ClN₄O
• 分子量: 266.73
• InChiKey: UJDLQTRREKUBPD-UHFFFAOYSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((6-chloro-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)morpholine 、 2-氟-4-氯-苄氯 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 2-甲基四氢呋喃 、 水 为溶剂， 反应 16.5h， 以50%的产率得到4-((6-chloro-3-(4-chloro-2-fluorobenzyl)-2-methylimidazo-[1,2-b]pyridazin-8-yl)methyl)morpholine
  参考文献：
  名称：

  Development of an Alternate Synthesis for a Key JAK2 Inhibitor Intermediate via Sequential C–H Bond Functionalization

  摘要：

  The development of an alternative synthetic route to a functionalized imidazopyridazine which strategically streamlines the synthesis and avoids a number of problematic reagents is described. Key to the success of this alternative route is the use of two C-H functionalization reactions: a Pd-catalyzed direct benzylation reaction to functionalize a C-H bond with a substituted benzyl group and a V-catalyzed NMO addition reaction to install a benzylic morpholine moiety.

  DOI：

  10.1021/op300344m
• 作为产物：
  描述：

  6-氯-2-甲基-咪唑并[2,1-f]吡嗪-3-羧酸乙酯 在 bis(acetylacetonate)oxovanadium 、 硫酸 作用下， 以 1,2-丙二醇 、 乙醇 、 水 为溶剂， 反应 66.0h， 生成 4-((6-chloro-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)morpholine
  参考文献：
  名称：

  Development of an Alternate Synthesis for a Key JAK2 Inhibitor Intermediate via Sequential C–H Bond Functionalization

  摘要：

  The development of an alternative synthetic route to a functionalized imidazopyridazine which strategically streamlines the synthesis and avoids a number of problematic reagents is described. Key to the success of this alternative route is the use of two C-H functionalization reactions: a Pd-catalyzed direct benzylation reaction to functionalize a C-H bond with a substituted benzyl group and a V-catalyzed NMO addition reaction to install a benzylic morpholine moiety.

  DOI：

  10.1021/op300344m

文献信息

• Development of an Alternate Synthesis for a Key JAK2 Inhibitor Intermediate via Sequential C–H Bond Functionalization
  作者：Alison N. Campbell、Kevin P. Cole、Joseph R. Martinelli、Scott A. May、David Mitchell、Patrick M. Pollock、Kevin A. Sullivan

  DOI：10.1021/op300344m

  日期：2013.2.15

  The development of an alternative synthetic route to a functionalized imidazopyridazine which strategically streamlines the synthesis and avoids a number of problematic reagents is described. Key to the success of this alternative route is the use of two C-H functionalization reactions: a Pd-catalyzed direct benzylation reaction to functionalize a C-H bond with a substituted benzyl group and a V-catalyzed NMO addition reaction to install a benzylic morpholine moiety.