(1r,4r)-4-((1,1-dimethylethyl)sulfonamido)cyclohexane-1-carbonyl chloride | 1195758-84-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1r,4r)-4-((1,1-dimethylethyl)sulfonamido)cyclohexane-1-carbonyl chloride
• CAS: 1195758-84-9
• 化学式: C₁₁H₂₀ClNO₃S
• 分子量: 281.804
• InChiKey: BXQVJRVQDZQJKE-KYZUINATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1r,4r)-4-((1,1-dimethylethyl)sulfonamido)cyclohexane-1-carbonyl chloride 在 四氯化钛 N-甲基咪唑 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 5-((1r,4r)-4-((1,1-dimethylethyl)sulfonamido)cyclohexyl)-1H-pyrazol-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  EP2280000

  摘要：

  公开号：
• 作为产物：
  描述：

  4-氨基环己羧酸 在 氯化亚砜 、 hexaammonium heptamolybdate tetrahydrate 、 水 、 双氧水 、 sodium methylate 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (1r,4r)-4-((1,1-dimethylethyl)sulfonamido)cyclohexane-1-carbonyl chloride
  参考文献：
  名称：

  Development of an Optimized Synthetic and Purification Process of S-2367 (Velneperit), a Novel Neuropeptide Y (NPY) Y5 Receptor Antagonist

  摘要：

  We developed a simple synthetic route to S-2367 (Velneperit) (1) using trans-1-ethoxycarbonyl-4-aminocyclohexane hydrochloride salt (12) as a starting material. The key step was Na2WO4/H2O2 oxidation, and we found that it was accelerated in weakly basic conditions. The finding was useful to control one of the critical impurities: 14 in 10. The new process was more efficient than the early process from the viewpoint of the number of reactions, yield, throughput, and EHS (environment, health, and safety) but a quality deviation occurred in the pilot manufacturing: 10 content in 1 was over the upper limit. The cause was presumed to be hydrolysis of 1 during the recrystallization step. After finding it, we developed two reliable purification processes. The first was slurry washing including clever polymorphic control using only acetone and water. The second was salt formation of 10 and rational building of the recrystallization procedure based on solubility to improve removal rate.

  DOI：

  10.1021/acs.oprd.5b00023

文献信息

• PROCESS FOR PRODUCTION OF COMPOUND HAVING ANTAGONISTIC ACTIVITY ON NPYY5 RECEPTOR, AND USEFUL CRYSTAL
  申请人：Sugata Yoshihide

  公开号：US20110060145A1

  公开（公告）日：2011-03-10

  Disclosed are process for producing a compound having NPYY5 receptor antagonism and useful crystals. A process for producing a compound represented by the formula (IV): wherein R 1 is substituted or unsubstituted alkyl, R 2 is substituted or unsubstituted alkyl, and n is 1 or 2, or the like, which comprises reacting a compound represented by the formula (II): wherein R 1 and n are as defined above, and X is a leaving group, or the like and a compound represented by formula (III): wherein R 2 is as defined above, or the like.

  本发明涉及一种具有NPYY5受体拮抗作用且有用的晶体的化合物制备过程。一种制备由公式(IV)表示的化合物的方法：其中R1是取代或未取代的烷基，R2是取代或未取代的烷基，n为1或2，或类似物，包括将由公式(II)表示的化合物：其中R1和n如上所定义，X是离去基团，或类似物，和由公式(III)表示的化合物反应：其中R2如上所定义，或类似物。