3-溴-5-氯吡唑[1,5-A]并嘧啶 | 960613-96-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 中文名称: 3-溴-5-氯吡唑[1,5-A]并嘧啶
• 中文别名: 3-溴-5-氯吡咯[1,5-A]并嘧啶；3-溴-5-氯吡唑并[1,5-A]嘧啶
• 英文名称: 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine
• CAS: 960613-96-1
• 化学式: C₆H₃BrClN₃
• 分子量: 232.467
• InChiKey: IYSBSUPWYUVHKG-UHFFFAOYSA-N

物化性质

• 密度：
  2.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 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，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-5-chloropyrazolo[1,5-a]pyrimidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Bromo-5-chloropyrazolo[1,5-a]pyrimidine
CAS number: 960613-96-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H3BrClN3
Molecular weight: 232.5

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

3-溴-5-氯吡唑[1,5-A]并嘧啶显示了与吡唑并[1,5-A]嘧啶-7(4H)-酮相似的许多特性，并且是多种化学抗炎和抗血吸虫药物的一部分。

反应信息

• 作为反应物：
  描述：

  3-溴-5-氯吡唑[1,5-A]并嘧啶 在 盐酸 、 4-二甲氨基吡啶 、 potassium phosphate 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.5h， 生成 2-[3-[5-[2-(Propan-2-ylamino)ethylamino]pyrazolo[1,5-a]pyrimidin-3-yl]phenoxy]acetic acid
  参考文献：
  名称：

  [EN] MACROCYCLIC LRRK2 KINASE INHIBITORS
  [FR] INHIBITEURS MACROCYCLIQUES DE LA KINASE LRRK2

  摘要：

  本发明涉及一类新颖的大环化合物，以及含有这些化合物的组合物，这些化合物作为激酶抑制剂，特别是作为LRRK2（富含亮氨酸的重复激酶2）的抑制剂。此外，本发明还提供了所述化合物的制备过程，以及它们的使用方法，例如作为药物或诊断剂，特别是用于治疗和/或诊断由LRRK2激酶活性特征引起的疾病，如神经系统疾病，包括帕金森病和阿尔茨海默病。

  公开号：

  WO2013046029A1
• 作为产物：
  描述：

  5-氯吡唑并[1,5-a]嘧啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以94%的产率得到3-溴-5-氯吡唑[1,5-A]并嘧啶
  参考文献：
  名称：

  吡唑并[1，5-a]嘧啶的优化导致鉴定出高度选择性的酪蛋白激酶2抑制剂。

  摘要：

  酪蛋白激酶2（CK2）是组成型表达的丝氨酸/苏氨酸激酶，具有大量的细胞底物。因此，CK2已经与多种调节功能相关，并且CK2的失调与疾病发展特别是与癌症有关。疾病病理学的广泛含义使CK2成为有吸引力的靶标。迄今为止，最先进的CK2抑制剂是silmitasertib，尽管已描述了silmitasertib的多个脱靶靶标，但已在临床试验中研究了silmitasertib。为了确定CK2抑制在癌症，其他疾病和正常生理中的作用，非常需要选择性CK2抑制剂的开发。在这项研究中，我们探索了吡唑并[1,5- a]嘧啶铰链结合部分用于开发选择性CK2抑制剂。该支架的优化（包括大环化）导致产生IC20（31），该化合物对CK2表现出较高的体外效力（K D  = 12 nM），对CK2的排他选择性更高。X射线分析揭示了IC20的典型I型结合模式（31）。但是，效力需要许多CK2抑制剂（包括silmitasert

  DOI：

  10.1016/j.ejmech.2020.112770
• 作为试剂：
  描述：

  5-氯吡唑并[1,5-a]嘧啶 、 溴 在 溶剂黄146 、 乙醚 、 crude product 、 水 、 异丙醇 、 正己烷 、 3-溴-5-氯吡唑[1,5-A]并嘧啶 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以to give 3-bromo-5-chloro-pyrazolo[1,5-a]pyrimidine [Intermediate A] (34.6 g, 49%)的产率得到3-溴-5-氯吡唑[1,5-A]并嘧啶
  参考文献：
  名称：

  PYRAZOLOPYRIMIDINES AND SALTS THEREOF, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, METHODS OF PREPARING SAME AND USES OF SAME

  摘要：

  本发明涉及一种通式(I)的吡唑吡咯啉化合物及其盐，涉及包含该吡唑吡咯啉化合物的制药组合物，以及制备该吡唑吡咯啉化合物的方法，以及将其用于制造用于治疗或预防异常血管生长病或伴随异常血管生长病的药物组合物的用途。

  公开号：

  US20080039455A1

文献信息

• [EN] PYRAZOLO[1,5-a]PYRIMIDINE-BASED COMPOUNDS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE<br/>[FR] COMPOSÉS À BASE DE PYRAZOLO[1,5-A] PYRIMIDINE, COMPOSITIONS LES COMPRENANT ET UTILISATIONS DE CEUX-CI
  申请人：LEXICON PHARMACEUTICALS INC

  公开号：WO2013134228A1

  公开（公告）日：2013-09-12

  Pyrazolo[1,5-a]pyrimidine-based compounds of the formula: are disclosed, wherein R1, R2 and R3 are defined herein. Compositions comprising the compounds and methods of their use to treat, manage and/or prevent diseases and disorders mediated by mediated by adaptor associated kinase 1 activity are also disclosed.

  基于吡唑并[1,5-a]嘧啶的化合物的公式如下：其中R1、R2和R3在此处被定义。还公开了包含这些化合物的组合物以及它们的使用方法，用于治疗、管理和/或预防由适配器相关激酶1活性介导的疾病和紊乱。
• [EN] MACROCYCLIC RIP2-KINASE INHIBITORS<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA RIP2-KINASE
  申请人：ONCODESIGN SA

  公开号：WO2021152165A1

  公开（公告）日：2021-08-05

  The present invention relates to macrocyclic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of RIP2-kinase, and/or mutants thereof, for use in the diagnosis, prevention and/or treatment of RIP2-kinase associated diseases. Moreover, the present invention provides methods of using said compounds, for instance as a medicine or diagnostic agent.

  本发明涉及作为激酶抑制剂，特别是作为RIP2激酶及其/或其突变体的抑制剂的大环化合物及其组合物，用于诊断、预防和/或治疗与RIP2激酶相关的疾病。此外，本发明提供了使用这些化合物的方法，例如作为药物或诊断剂。
• [EN] MACROCYCLIC SALT-INDUCIBLE KINASE INHIBITORS<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA KINASE INDUCTIBLE PAR UN SEL
  申请人：ONCODESIGN SA

  公开号：WO2014140313A1

  公开（公告）日：2014-09-18

  The present invention relates to macrocyclic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of SIK kinase, more in particular SIK1, SIK2 and/or SIK3 and/or mutants thereof, for use in the diagnosis, prevention and/or treatment of SIK-kinase associated diseases. Moreover, the present invention provides methods of using said compounds, for instance as a medicine or diagnostic agent.

  本发明涉及大环化合物以及含有作为激酶抑制剂，特别是SIK激酶抑制剂，尤其是SIK1、SIK2和/或SIK3以及/或其突变体的所述化合物的组合物，用于诊断、预防及/或治疗与SIK激酶相关的疾病。此外，本发明还提供了使用所述化合物的方法，例如作为药物或诊断剂。
• [EN] MACROCYCLIC FLT3 KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE FLT3 MACROCYCLIQUES
  申请人：ONCODESIGN SA

  公开号：WO2013045653A1

  公开（公告）日：2013-04-04

  The present invention relates to macrocylic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of FLT3 (FMS-Related Tyrosine kinase 3). Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine, in particular for the treatment of cell proliferative disorders, such as cancer.

  本发明涉及大环化合物以及含有作为激酶抑制剂，特别是FLT3（FMS相关酪氨酸激酶3）抑制剂的所述化合物的组合物。此外，本发明还提供了所述化合物的制备过程，以及使用它们的方法，例如作为药物，特别用于治疗细胞增殖紊乱，如癌症。
• MACROCYCLIC FLT3 KINASE INHIBITORS
  申请人：ONCODESIGN S.A.

  公开号：US20140303159A1

  公开（公告）日：2014-10-09

  The present invention relates to macrocylic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of FLT3 (FMS-Related Tyrosine kinase 3). Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine, in particular for the treatment of cell proliferative disorders, such as cancer.

  本发明涉及大环化合物以及含有作为激酶抑制剂，特别是FLT3（FMS相关酪氨酸激酶3）抑制剂的所述化合物的组合物。此外，本发明还提供了所述化合物的制备过程，以及使用它们的方法，例如作为药物，特别用于治疗细胞增殖紊乱，如癌症。