tert-butyl N-(1,3-benzodioxol-5-ylmethyl)-N-(2-bromoethyl)carbamate | 938168-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: tert-butyl N-(1,3-benzodioxol-5-ylmethyl)-N-(2-bromoethyl)carbamate
• CAS: 938168-32-2
• 化学式: C₁₅H₂₀BrNO₄
• 分子量: 358.232
• InChiKey: UKSBHWWIGCHLAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(1,3-benzodioxol-5-ylmethyl)-N-(2-bromoethyl)carbamate 在 盐酸 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-(1,3-benzodioxol-5-ylmethyl)-4-(2-imidazol-1-yl-6-methylpyrimidin-4-yl)butan-1-amine
  参考文献：
  名称：

  Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors

  摘要：

  We have identified and synthesized a series of imidazole containing dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated and SAR studies led to the identification of compound 35, which showed a dose dependant inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.112
• 作为产物：
  描述：

  胡椒醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 isopropyl alcohol 为溶剂， 反应 4.0h， 生成 tert-butyl N-(1,3-benzodioxol-5-ylmethyl)-N-(2-bromoethyl)carbamate
  参考文献：
  名称：

  Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors

  摘要：

  We have identified and synthesized a series of imidazole containing dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated and SAR studies led to the identification of compound 35, which showed a dose dependant inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.112

文献信息

• Methods of Preparing 2-Imidazol-1-Yl-4-Methyl-6-Pyrrolidin-2-Yl-Pyrimidine and 4-(1-Alkylpyrrolidin-2-Yl)-2-(1H-Imidazol-1-Yl)-6-Methylpyrimidine Derivatives
  申请人：Cousins Russell D.

  公开号：US20080293942A1

  公开（公告）日：2008-11-27

  The present invention is directed to a novel, high yield method for preparing 2-imidazol-1-yl-4-methyl-6-pyrrolidin-2-yl-pyrimidine, particularly to a method of preparing 4-(1-alkylpyrrolidin-2-yl)-2-(1H-imidazol-1-yl)-6-methylpyrimidine, more particularly, 2-(2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)pyrrolidrn-1-yl)-N-(benzo[d][1,3]dioxol-5-yh-nethyl)-N-methylethanamine. These compounds and pharmaceutical compositions thereof are inhibitors of nitric oxide synthase, are selective for inducible nitric oxide synthase, and are useful in treating diseases and disorders including inflammation and pain.

  本发明涉及一种新的高产率制备2-咪唑-1-基-4-甲基-6-吡咯烷-2-基嘧啶的方法，特别是一种制备4-(1-烷基吡咯烷-2-基)-2-(1H-咪唑-1-基)-6-甲基嘧啶的方法，更特别地，2-(2-(2-(1H-咪唑-1-基)-6-甲基嘧啶-4-基)吡咯烷-1-基)-N-(苯并[d][1,3]二噁烷-5-基-甲基)-N-甲基乙胺。这些化合物及其药物组成物是一氧化氮合酶抑制剂，对诱导型一氧化氮合酶具有选择性，可用于治疗炎症和疼痛等疾病和障碍。
• [EN] METHODS OF PREPARING 2-IMIDAZOL-1-YL-4-METHYL-6-PYRROLIDIN-2-YL-PYRIMIDINE AND 4-(1-ALKYLPYRROLIDIN-2-YL)-2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDINE DERIVATIVES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE LA 2-IMIDAZOL-1-YL-4-METHYL-6-PYRROLIDIN-2-YL-PYRIMIDINE ET 4-(1-ALKYL PYRROLIDIN-2-YL)-2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDINE
  申请人：KALYPSYS INC

  公开号：WO2007062417A1

  公开（公告）日：2007-05-31

  [EN] The present invention is directed to a novel, high yield method for preparing 2-imidazol-l-yl-4- methyl-6-?yrrolidin-2-yl-pyrimidine, particularly to a method of preparing 4-(l-alkylpyrrolidin-2-yl)-2- (lH-imidazol-l-yl)-6-methylpyrimidine, more particularly, 2-(2-(2-(lH-imidazol-l-yl)-6- methylpyrimidin-4-yl)pyrrolidrn-l-yl)-N-(benzo[d][l,3]dioxol-5-yhnethyl)-N-methylethanamine. These compounds and pharmaceutical compositions thereof are inhibitors of nitric oxide synthase, are selective for inducible nitric oxide synthase, and are useful in treating diseases and disorders including inflammation and pain.
  [FR] La présente invention concerne un procédé innovant à haut rendement pour la préparation de la 2-imidazol-1-yl-4-méthyl-6-?yrrolidin-2-yl-pyrimidine, en particulier un procédé de préparation de la 4-(1-alkylpyrrolidin-2-yl)-2-(1H-imidazol-1-yl)-6-méthylpyrimidine et plus particulièrement un procédé de préparation de la 2-(2-(2-(1H-imidazol-1-yl)-6-méthylpyrimidin-4-yl) pyrrolidin-1-yl)-N-(benzo[d][1,3]dioxol-5-ylméthyl)-N-méthyléthanamine. Ces composés et les compositions pharmaceutiques de ceux-ci sont des inhibiteurs de l'oxyde nitrique-synthase, ils sont sélectifs de l'oxyde nitrique-synthase inductible et ils sont utilisables pour le traitement de maladies et de troubles, y compris l'inflammation et la douleur.