3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶 | 405224-24-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 中文名称: 3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶
• 中文别名: 5-溴-1H-吡唑并[3,4-B]吡啶-3-胺
• 英文名称: 5-bromo-1H-pyrazolo[3,4-b]pyridin-3-amine
• 英文别名: 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-amine；3-amino-5-bromo-1H-pyrazolo[3,4-b]pyridine；5-bromo-2H-pyrazolo[3,4-b]pyridin-3-amine
• CAS: 405224-24-0
• 化学式: C₆H₅BrN₄
• mdl: MFCD08059261
• 分子量: 213.037
• InChiKey: SSNUTEUZXZIYTB-UHFFFAOYSA-N

物化性质

• 沸点：
  429.1±40.0 °C(Predicted)
• 密度：
  1.994

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 危险性防范说明：
  P261,P305+P351+P338

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-bromo-1H-pyrazolo[3,4-b]pyridin-3-amine
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: 5-bromo-1H-pyrazolo[3,4-b]pyridin-3-amine
CAS number: 405224-24-0

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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: C6H5BrN4
Molecular weight: 213.0

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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 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-氨基-5-溴-1H-吡唑并[3,4-B]吡啶是一种有机中间体。

制备

3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶可由2-氯烟腈为原料，按以下步骤制备：

步骤１：2-甲氧基-烟腈

将4.98克（217毫摩尔）钠加入至80毫升无水甲醇中，室温搅拌反应介质10分钟。随后在0℃下加入10克（72.2毫摩尔）2-氯烟腈，于25℃继续搅拌反应混合物16小时。将该反应缓慢用水解离，然后在室温下过滤沉淀物，并用冷水冲洗。最后，在50℃干燥下得到黄色固体形式的2-甲氧基-烟腈7.85克（收率81％）。

步骤２：5-溴-2-甲氧基-烟腈

在0℃下，依次加入12.23克（149毫摩尔）乙酸钠和7.66毫升（149毫摩尔）溴至10克（74.6毫摩尔）2-甲氧基-烟腈的29毫升乙酸溶液中。将反应混合物于70℃加热过夜。在室温下，将反应介质加入冰浴中并过滤沉淀物，用冷水冲洗后，在50℃干燥下得到白色固体形式的11.6克（收率73％）5-溴-2-甲氧基烟腈。

步骤３：3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶

在室温下，将35毫升（23.47毫摩尔）肼加入至5克（23.47毫摩尔）5-溴-2-甲氧基烟腈中。保持反应介质于100℃3小时。返回至室温后，过滤沉淀物，并用水冲洗。最后，在50℃干燥下得到黄色固体形式的3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶3.6克（收率72％）。

反应信息

• 作为反应物：
  描述：

  3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶 在 吡啶 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium acetate 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)butyramide
  参考文献：
  名称：

  5-Aryl-pyrazolo[3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3)

  摘要：

  A novel series of pyrazolo[3,4-b]pyridines has been identified that are potent inhibitors of glycogen synthase kinase-3 (GSK-3). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00134-3
• 作为产物：
  描述：

  3-氰基-2-甲氧基吡啶 在 溴 、 sodium acetate 、 溶剂黄146 、 肼 作用下， 反应 3.0h， 生成 3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶
  参考文献：
  名称：

  DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE AS MEDICAMENT

  摘要：

  本发明涉及以下式（I）的化合物： 或其药学上可接受的盐或溶剂，同分异构体，立体异构体或同分异构体的混合物，比如对映体混合物，尤其是消旋混合物；以及将其用作药物，尤其是用于治疗癌症、炎症和神经退行性疾病如阿尔茨海默病；将其用作激酶抑制剂；含有同样化合物的药物组合物；以及制备同样化合物的方法。

  公开号：

  US20130085144A1
• 作为试剂：
  描述：

  5-溴-2-氯烟腈 、 肼 在 碳酸氢钠 、 水 、 3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶 作用下， 以 正丁醇 为溶剂， 反应 14.0h， 生成 3-氨基-5-溴-1H-吡唑并[3,4-B]吡啶
  参考文献：
  名称：

  Heterocyclic inhibitors of c-Met and uses thereof

  摘要：

  本发明提供了一些化合物，用作c-Met酪氨酸激酶的抑制剂。本发明还提供了含有本发明化合物的药学上可接受的组合物，并提供了使用这些组合物治疗各种增殖性疾病的方法。

  公开号：

  US08481538B2

文献信息

• [EN] BIARYL ACETAMIDE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE BIARYLE ACÉTAMIDE ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：AMBIT BIOSCIENCES CORP

  公开号：WO2015031613A1

  公开（公告）日：2015-03-05

  Biaryl acetamide compounds and compositions and their methods of use are provided for modulating the activity of class III receptor tyrosine kinases and for the treatment, prevention or amelioration of one or more symptoms of disease of disorder mediated by class III receptor tyrosine kinases.

  双芳基乙酰胺化合物及其组合物以及它们的使用方法被提供用于调节III类受体酪氨酸激酶的活性，以及用于治疗、预防或改善由III类受体酪氨酸激酶介导的疾病或紊乱的一个或多个症状。
• DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE AS MEDICAMENT
  申请人：PIERRE FABRE MEDICAMENT

  公开号：US20130085144A1

  公开（公告）日：2013-04-04

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture; as well as to the use of same as a drug, notably intended for the treatment of cancer, inflammation and neurodegenerative diseases such as Alzheimer's disease; to the use of same as a kinase inhibitor; to the pharmaceutical compositions comprising same; and to methods for the preparation of same.

  本发明涉及以下式（I）的化合物： 或其药学上可接受的盐或溶剂，同分异构体，立体异构体或同分异构体的混合物，比如对映体混合物，尤其是消旋混合物；以及将其用作药物，尤其是用于治疗癌症、炎症和神经退行性疾病如阿尔茨海默病；将其用作激酶抑制剂；含有同样化合物的药物组合物；以及制备同样化合物的方法。
• [EN] DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE FOR TREATING PAIN<br/>[FR] DÉRIVÉS DE TYPE AZA-INDAZOLE OU DIAZA-INDAZOLE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：PF MEDICAMENT

  公开号：WO2014016433A1

  公开（公告）日：2014-01-30

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture; for use in the treatment of pain.

  本发明涉及如下式(I)的化合物：或其药用可接受的盐或溶剂化物，其构象异构体，或其立体异构体或立体异构体混合物，以任何比例，例如对映体混合物，尤其是外消旋混合物；用于治疗疼痛。
• [EN] DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE FOR TREATING A CANCER OVEREXPRESSING TRK<br/>[FR] DÉRIVÉS DE TYPE AZA-INDAZOLE OU DIAZA-INDAZOLE POUR LE TRAITEMENT D'UN CANCER SUREXPRIMANT LA TRK
  申请人：PF MEDICAMENT

  公开号：WO2014016434A1

  公开（公告）日：2014-01-30

  The present invention relates to a compound of following formula (I) or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture, as well as pharmaceutical composition comprising such a compound, for use in the treatment of a cancer associated with the overexpression of at least one Trk protein.

  本发明涉及式(I)所示的化合物，或其药用可接受的盐或溶剂化物，其同分异构体，或其立体异构体或立体异构体混合物，以任何比例，例如对映体混合物，尤其是外消旋混合物，以及包含该化合物的药物组合物，用于治疗与至少一种Trk蛋白过表达相关的癌症。
• Derivatives of azaindazole or diazaindazole type for treating a cancer overexpressing trk
  申请人：PIERRE FABRE MEDICAMENT

  公开号：EP2689779A1

  公开（公告）日：2014-01-29

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture, as well as pharmaceutical composition comprising such a compound, for use in the treatment of a cancer associated with the overexpression of at least one Trk protein.

  本发明涉及具有以下公式(I)的化合物： 或其药用可接受的盐或溶剂化物，其互变异构体，或其立体异构体或立体异构体混合物，以任何比例，如对映体混合物，尤其是外消旋混合物，以及包含该化合物的药物组合物，用于治疗与至少一种Trk蛋白过度表达相关的癌症。