3-氨基-4,5-二氯吡啶 | 89284-39-9

• 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
• 中文名称: 3-氨基-4,5-二氯吡啶
• 英文名称: 4,5-dichloro-pyridin-3-ylamine
• 英文别名: 3-amino-4,5-dichloropyridine；3-Amino-4,5-dichlor-pyridin；3-Amino-4,5-dichlorpyridin；4,5-Dichloropyridin-3-amine
• CAS: 89284-39-9
• 化学式: C₅H₄Cl₂N₂
• mdl: MFCD09910182
• 分子量: 163.006
• InChiKey: AYLFZJLTKYILPZ-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C
• 沸点：
  279.6±35.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  3-氨基-4,5-二氯吡啶 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.25h， 生成 9-butyl-8-(7-chlorothiazolo[4,5-c]pyridin-2-ylsulfanyl)-9H-purin-6-ylamine
  参考文献：
  名称：

  7‘-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors

  摘要：

  We report on the discovery of benzo- and pyridino-thiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7'-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chlorobenzothiazol-2- ylsulfanyl)-9-(2-cyclopropylamino-ethyl)-9H-purin-6-ylamine).

  DOI：

  10.1021/jm051146h
• 作为产物：
  描述：

  4-羟基-3-硝基吡啶 在 盐酸 、 氯 、 溶剂黄146 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.83h， 生成 3-氨基-4,5-二氯吡啶
  参考文献：
  名称：

  7‘-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors

  摘要：

  We report on the discovery of benzo- and pyridino-thiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7'-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chlorobenzothiazol-2- ylsulfanyl)-9-(2-cyclopropylamino-ethyl)-9H-purin-6-ylamine).

  DOI：

  10.1021/jm051146h

文献信息

• N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide herbicides
  申请人：DowElanco

  公开号：US05571775A1

  公开（公告）日：1996-11-05

  Substituted N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide compounds, such as N-(2,6-difluorophenyl)-5-methoxy-7-methyl[1,2,4]triazolo[1,5-a]pyridine-2- sulfonamide, N-(4-bromo-1-methyl-3-pyrazoly)-8-chloro-5-methoxy[1,2,4]triazolo[1,5-a]py ridine-2-sulfonamide, and N-(2-fluoro-4-methyl-3-pyridinyl)-8-ethoxy-6-chloro[1,2,4]triazolo[1,5-a]- pyridine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-a]pyridine compound with an aryl amine. The compounds prepared were found to possess excellent herbicidal activity on a broad spectrum of vegetation at low application rates.

  取代的N-芳基[1,2,4]三唑并[1,5-a]吡啶-2-磺胺化合物，例如N-(2,6-二氟苯基)-5-甲氧基-7-甲基[1,2,4]三唑并[1,5-a]吡啶-2-磺胺、N-(4-溴-1-甲基-3-吡唑基)-8-氯-5-甲氧基[1,2,4]三唑并[1,5-a]吡啶-2-磺胺和N-(2-氟-4-甲基-3-吡啶基)-8-乙氧基-6-氯[1,2,4]三唑并[1,5-a]吡啶-2-磺胺，通过将2-氯磺酰[1,2,4]三唑并[1,5-a]吡啶化合物与芳基胺缩合而制备。所制备的化合物在低施用率下对广谱植被具有出色的除草活性。
• N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
  申请人：DowElanco

  公开号：US05614469A1

  公开（公告）日：1997-03-25

  Substituted N-pyridinyl[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide compounds, such as N-(2-fluoro-4-methyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide, were prepared bycondensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminopyridine compound, such as 3-amino-2-fluoro-4-methylpyridine, and found to possess herbicidal utility.

  已合成N-吡啶基[1,2,4]三唑[1,5-c]-嘧啶-2-磺酰胺类化合物，例如N-(2-氟-4-甲基)-7-氟-5-甲氧基[1,2,4]三唑[1,5-c]嘧啶-2-磺酰胺，通过将2-氯磺酰基[1,2,4]三唑[1,5-c]嘧啶类化合物（例如2-氯磺酰基-7-氟-5-甲氧基[1,2,4]三唑[1,5-c]嘧啶）与取代的3-氨基吡啶类化合物（例如3-氨基-2-氟-4-甲基吡啶）缩合而成，并发现具有除草作用。
• N-aryl\x9b1,2,4!triazolo\x9b1,5-a!pyridine-2-sulfonamide herbicides
  申请人：DowElanco

  公开号：US05700940A1

  公开（公告）日：1997-12-23

  Substituted N-aryl\x9b1,2,4!triazolo\x9b1,5-a!pyridine-2-sulfonamide compounds, such as N-(2,6-difluorophenyl)-5-methoxy-7-methyl\x9b1,2,4!triazolo\x9b1,5-a!pyridine-2- sulfonamide, N-(4-bromo-1-methyl-3-pyrazolyl)-8-chloro-5-methoxy\x9b1,2,4!triazolo\x9b1,5-a!p yridine-2-sulfonamide, and N-(2-fluoro-4-methyl-3-pyridinyl)-8-ethoxy-6-chloro\x9b1,2,4!triazolo\x9b1,5-a!p yridine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl\x9b1,2,4!triazolo\x9b1,5-a!pyridine compound with an aryl amine. The compounds prepared were found to possess excellent herbicidal activity on a broad spectrum of vegetation at low application rates.

  替代的N-芳基[1,2,4]三唑[1,5-a]吡啶-2-磺酰胺化合物，例如N-(2,6-二氟苯基)-5-甲氧基-7-甲基[1,2,4]三唑[1,5-a]吡啶-2-磺酰胺，N-(4-溴-1-甲基-3-吡唑基)-8-氯-5-甲氧基[1,2,4]三唑[1,5-a]吡啶-2-磺酰胺和N-(2-氟-4-甲基-3-吡啶基)-8-乙氧基-6-氯[1,2,4]三唑[1,5-a]吡啶-2-磺酰胺，通过2-氯磺酰[1,2,4]三唑[1,5-a]吡啶化合物与芳基胺缩合而成。发现所制备的化合物在低施用量下对广谱植被具有出色的除草活性。
• Orally Active Purine-Based Inhibitors of Heat Shock Protein 90
  申请人：Kasibhatla R. Srinivas

  公开号：US20070129334A1

  公开（公告）日：2007-06-07

  Novel purine compounds and tautomers and pharmaceutically acceptable salts thereof are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same. Methods of using the novel purine compounds of the invention, and tautomers and pharmaceutically acceptable salts thereof, include their use in inhibiting heat shock protein 90's (HSP90's) to thereby treat or prevent HSP90-dependent diseases, e.g., proliferative disorders such as breast cancer.

  本发明描述了新型嘌呤化合物及其互变异构体和药学上可接受的盐，以及包含它们的制药组合物、包含它们的复合物（例如HSP90复合物）和使用它们的方法。使用本发明的新型嘌呤化合物、互变异构体和药学上可接受的盐的方法包括在抑制热休克蛋白90（HSP90）中使用它们，从而治疗或预防HSP90依赖性疾病，例如增生性疾病如乳腺癌。
• 2-Benzylthio-8-amino(1,2,4)triazolo(1,5-pyridines
  申请人：Dow AgroSciences LLC

  公开号：EP0972774A2

  公开（公告）日：2000-01-19

  The invention relates to 2-benzylthio-8-amino[1,2,4]triazolo[1,5-a]pyridines and a process for the preparation thereof. These compounds can be used for the preparation of 2-benzylthio[1,2,4]triazolo[1,5-a]pyridine compounds, which are important intermediates in the preparation of N-aryl[1,2,4]triazolo[1,5-a]pyridines. The reaction is generally carried out by combining one molar equivalent of a 2-benzylthio-8-chloro[1,2,4]triazolo[1,5-a]pyridine compound with at least 3 molar equivalents of stannous chloride, one molar equivalent of stannic chloride, and an excess of hydrogen chloride or at least one molar equivalent of the alcohol.

  本发明涉及 2-苄硫基-8-氨基[1,2,4]三唑并[1,5-a]吡啶及其制备工艺。这些化合物可用于制备 2-苄硫基[1,2,4]三唑并[1,5-a]吡啶化合物，后者是制备 N-芳基[1,2,4]三唑并[1,5-a]吡啶的重要中间体。 该反应一般通过将 1 摩尔当量的 2-苄硫基-8-氯[1,2,4]三唑并[1,5-a]吡啶化合物与至少 3 摩尔当量的氯化亚锡、1 摩尔当量的氯化锡和过量的氯化氢或至少 1 摩尔当量的醇结合进行。