6-chloro-4-(o-tolyl)pyridazin-3-amine | 1466574-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-chloro-4-(o-tolyl)pyridazin-3-amine
• 英文别名: 6-chloro-4-o-tolylpyridazin-3-ylamine；6-Chloro-4-o-tolylpyridazin-3-ylamine；6-chloro-4-(2-methylphenyl)pyridazin-3-amine
• CAS: 1466574-47-9
• 化学式: C₁₁H₁₀ClN₃
• 分子量: 219.673
• InChiKey: WLEBRAXESJBJCE-UHFFFAOYSA-N

物化性质

• 沸点：
  414.6±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙氧基乙胺 、 6-chloro-4-(o-tolyl)pyridazin-3-amine 在 2-(二环己基膦)3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯 、 Brettphos palladacycle 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以81%的产率得到N3-(2-ethoxyethyl)-5-(o-tolyl)pyridazine-3,6-diamine
  参考文献：
  名称：

  Facile synthesis of 4-aryl and alkyl substituted, N 6 -alkylated pyridazine-3,6-diamines

  摘要：

  Substituted pyridazine-3,6-diamines are attractive but poorly precedented scaffolds in medicinal chemistry and are challenging targets in terms of synthetic tractability. In the following communication we report the use of a Buchwald protocol for the facile synthesis of 4-aryl and alkyl substituted, N-6-alkylated pyridazine-3,6-diamines. This approach utilises the unreactive nature of the pyridazine 3-amino group, negating the need for an additional protecting group in the transformation. The relevant precursors were prepared by selective Suzuki or Negishi transformations using commercially available 4-bromo-6-chloro-3-pyridazinamine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.075
• 作为产物：
  描述：

  3-氨基-4-溴-6-氯哒嗪 、 2-甲基苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以43%的产率得到6-chloro-4-(o-tolyl)pyridazin-3-amine
  参考文献：
  名称：

  Facile synthesis of 4-aryl and alkyl substituted, N 6 -alkylated pyridazine-3,6-diamines

  摘要：

  Substituted pyridazine-3,6-diamines are attractive but poorly precedented scaffolds in medicinal chemistry and are challenging targets in terms of synthetic tractability. In the following communication we report the use of a Buchwald protocol for the facile synthesis of 4-aryl and alkyl substituted, N-6-alkylated pyridazine-3,6-diamines. This approach utilises the unreactive nature of the pyridazine 3-amino group, negating the need for an additional protecting group in the transformation. The relevant precursors were prepared by selective Suzuki or Negishi transformations using commercially available 4-bromo-6-chloro-3-pyridazinamine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.075

文献信息

• 1,2-PYRIDAZINES, 1,6-PYRIDAZINES AND PYRIMIDINES
  申请人：HOFFMANN-LA ROCHE INC.

  公开号：US20130267519A1

  公开（公告）日：2013-10-10

  This invention relates to novel 1,2-pyridazines, 1,6-pyridazines or pyrimidines of the formula wherein B 1 to B 3 and R 1 to R 7 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are GPBAR1 agonists and may therefore be useful as medicaments for the treatment of diseases such as type II diabetes.

  本发明涉及新颖的1,2-吡啶嗪、1,6-吡啶嗪或嘧啶的化合物，其化学式如下，其中B1至B3和R1至R7如描述和索赔中所定义，并且其药学上可接受的盐。这些化合物是GPBAR1激动剂，因此可能用作治疗疾病如2型糖尿病的药物。
• [EN] 1,2- PYRIDAZINE, 1,6- PYRIDAZINE OR PYRIMIDINE - BENZAMIDE DERIVATIVES AS GPBAR1 MODULATORS<br/>[FR] DÉRIVÉS DE 1,2-PYRIDAZINE, 1,6-PYRIDAZINE OU PYRIMIDINE-BENZAMIDE COMME MODULATEURS DE GPBAR1
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013149977A1

  公开（公告）日：2013-10-10

  This invention relates to novel 1,2-pyridazines, 1,6-pyridazines or pyrimidines of the formula I wherein B1 to B3 and R1 to R7 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are GPBAR1 agonists and may therefore be useful as medicaments for the treatment of diseases such as type II diabetes.

  本发明涉及新颖的1,2-吡啶嗪、1,6-吡啶嗪或式I中的嘧啶，其中B1至B3和R1至R7如描述和权利要求中所定义，并且其药学上可接受的盐。这些化合物是GPBAR1激动剂，因此可能用作治疗疾病如2型糖尿病的药物。
• 1,2-pyridazines, 1,6-pyridazines and pyrimidines
  申请人：Hoffman-La Roche Inc.

  公开号：US08748434B2

  公开（公告）日：2014-06-10

  This invention relates to novel 1,2-pyridazines, 1,6-pyridazines or pyrimidines of the formula wherein B1 to B3 and R1 to R7 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are GPBAR1 agonists and may therefore be useful as medicaments for the treatment of diseases such as type II diabetes.

  本发明涉及新型的1,2-吡啶嗪、1,6-吡啶嗪或嘧啶的化合物，其化学式如下： 其中B1至B3和R1至R7在说明书和权利要求书中定义，以及其药学上可接受的盐。这些化合物是GPBAR1激动剂，因此可能作为治疗二型糖尿病等疾病的药物有用。
• 1,2- PYRIDAZINE, 1,6- PYRIDAZINE OR PYRIMIDINE - BENZAMIDE DERIVATIVES AS GPBAR1 MODULATORS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2834226A1

  公开（公告）日：2015-02-11
• 1,2-PYRIDAZINE, 1,6-PYRIDAZINE OR PYRIMIDINE-BENZAMIDE DERIVATIVES AS GPBAR1 MODULATORS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2834226B1

  公开（公告）日：2016-05-25