5-溴-6-氟吡啶-2-胺 | 944401-65-4

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-溴-6-氟吡啶-2-胺
• 英文名称: 5-bromo-6-fluoropyridin-2-amine
• 英文别名: 2-amino-5-bromo-6-fluoropyridine
• CAS: 944401-65-4
• 化学式: C₅H₄BrFN₂
• 分子量: 191.003
• InChiKey: SJXWFNBZBXZDCL-UHFFFAOYSA-N

物化性质

• 沸点：
  245℃
• 密度：
  1.813
• 闪点：
  102℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体环境中，避免光照。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Amino-3-bromo-2-fluoropyridine
Synonyms: 5-Bromo-6-fluoropyridin-2-amine

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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: 6-Amino-3-bromo-2-fluoropyridine
CAS number: 944401-65-4

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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, refrigerated.
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: C5H4BrFN2
Molecular weight: 191.0

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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 fluoride, 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

2-氨基-5-溴-6-氟吡啶是一种有机中间体，可以通过将6-氟吡啶-2-胺进行溴代制备得到。

制备

在0℃下，将6-氟吡啶-2-胺（AlfaAesar，WardH，MA，5.16g，46.0mmol）溶解于CAN（230mL）中并搅拌。随后，在30分钟内通过加料漏斗将其溶于CAN（100mL）中的NBS（8.19g，46.0mmol）溶液中。加完后，继续搅拌30分钟。反应混合物在减压下浓缩，并将残余物溶解在DCM（20mL）中，然后吸附于硅胶上。通过色谱纯化（硅胶，0-75％EtOAc的己烷溶液），得到2-氨基-5-溴-6-氟吡啶，为白色泡沫状物质。实际产率为7.6g，39.8mmol，收率86%。1HNMR（400MHz，MeOH-d4）δppm7.59（1H，t，J=8.9Hz），6.32（1H，dd，J=8.5，1.5Hz）。m/z（ESI+）191.0（M+H）+。

反应信息

• 作为反应物：
  描述：

  5-溴-6-氟吡啶-2-胺 在 三丁基膦 、 palladium diacetate 、 sodium cyanoborohydride 、 caesium carbonate 、 溶剂黄146 、 copper(I) bromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 6-fluoro-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine
  参考文献：
  名称：

  Synthesis and evaluation of pyridylbenzofuran, pyridylbenzothiazole and pyridylbenzoxazole derivatives as 18F-PET imaging agents for β-amyloid plaques

  摘要：

  The synthesis and SAR of new beta-amyloid binding agents are reported. Evaluation of important properties for achieving good signal-to-background ratio is described. Compounds 27, 33, and 36 displayed desirable lipophilic and pharmacokinetic properties. Compound 27 was further evaluated with autoradiographic studies in vitro on human brain tissue and in vivo in Tg2576 mice. Compound 27 showed an increased signal-to-background ratio compared to flutemetamol 4, indicating its suitability as PET ligand for b-amyloid deposits in AD patients. The preparation of the corresponding F-18-labeled PET radioligand of compound 27 is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.011
• 作为产物：
  描述：

  2-氨基-6-氟吡啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以73%的产率得到5-溴-6-氟吡啶-2-胺
  参考文献：
  名称：

  Carbon-14 radiosynthesis of the benzofuran derivative andβ-amyloid plaque neuroimaging positron emission tomography radioligand AZD4694

  摘要：

  为了支持代谢物研究，从放射性标记的二氧化碳开始，经过 10 个放射合成步骤，用碳-14 标记了 β 淀粉样斑块神经影像正电子发射断层扫描放射性配体 AZD4694。在苯并呋喃杂环中标记的[14C]AZD4694的比活度为2.1 GBq/mmol，放射化学纯度大于99%。所述合成方法是碳-14 标记取代苯并呋喃的通用方法。

  DOI：

  10.1002/jlcr.3029

文献信息

• INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF
  申请人：Shire Human Genetic Therapies, Inc.

  公开号：US20190284182A1

  公开（公告）日：2019-09-19

  The present invention provides compounds and compositions thereof which are useful as inhibitors of plasma kallikrein and which exhibit desirable characteristics for the same.

  本发明提供了作为血浆激肽酶抑制剂并具有相同理想特性的化合物和组合物。
• HPK1 ANTAGONISTS AND USES THEREOF
  申请人：Nimbus Saturn, Inc.

  公开号：US20210078996A1

  公开（公告）日：2021-03-18

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物用于抑制HPK1和治疗HPK1介导的疾病的方法。
• [EN] SMALL MOLECULE MODULATORS OF IL-17<br/>[FR] MODULATEURS À PETITES MOLÉCULES D'IL-17
  申请人：LEO PHARMA AS

  公开号：WO2021250194A1

  公开（公告）日：2021-12-16

  The present invention relates to a compound according to formula (I), (I) and pharmaceutically acceptable salts, hydrates, or solvates thereof. The invention further relates to said compounds for use in therapy, to pharmaceutical compositions comprising said compounds, to methods of treating diseases, e.g. dermal diseases, with said compounds, and to the use of said compounds in the manufacture of medicaments.

  本发明涉及一种符合式(I)的化合物，以及其药学上可接受的盐、水合物或溶剂合物。该发明还涉及上述化合物在治疗中的应用，包括包含该化合物的药物组合物，用于使用该化合物制造药物的方法，例如用于治疗皮肤病等疾病的方法。
• Novel 2-Heteroaryl Substituted Benzothiophenes and Benzofuranes 709
  申请人：Arzel Erwan

  公开号：US20080221149A1

  公开（公告）日：2008-09-11

  The present invention relates to novel 2-heteroaryl substituted benzothiophene and benzofuran derivatives, precursors thereof, and therapeutic uses of such compounds, having the structural formula (Ia) below: and to their pharmaceutically acceptable salt, compositions and methods of use. Furthermore, the invention relates to novel 2-heteroaryl substituted benzothiophene and benzofuran derivatives that are suitable for imaging amyloid deposits in living patients, their compositions, methods of use and processes to make such compounds. More specifically, the present invention relates to a method of imaging amyloid deposits in brain in vivo to allow antemortem diagnosis of Alzheimer's disease as well as measureing clinical efficacy of Alzheimer's disease therapeutic agents.

  本发明涉及新型2-杂环芳基取代苯并噻吩和苯并呋喃衍生物，其前体以及这些化合物的治疗用途，具有如下结构式(Ia)： 以及它们的药用盐、组合物和使用方法。此外，本发明涉及适用于在活体患者中成像淀粉样沉积物的新型2-杂环芳基取代苯并噻吩和苯并呋喃衍生物，它们的组合物、使用方法以及制备这类化合物的过程。更具体地，本发明涉及一种在体内成像脑部淀粉样沉积物的方法，以允许在死前诊断阿尔茨海默病，并测量阿尔茨海默病治疗药物的临床疗效。
• [EN] 8-[6-[3-(AMINO)PROPOXY]-3-PYRIDYL]-1 -ISOPROPYL-IMIDAZO[4,5-C]QUINOLIN-2-ONE DERIVATIVES AS SELECTIVE MODULATORS OF ATAXIA TELANGIECTASIA MUTATED (ATM) KINASE FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS 8-[6-[3-(AMINO)PROPOXY]-3-PYRIDYL]-1-ISOPROPYL-IMIDAZO[4,5-C]QUINOLÉIN-2-ONE UTILISÉS EN TANT QUE MODULATEURS SÉLECTIFS DE L'ATAXIE TÉLANGIECTASIE MUTÉE (ATM) KINASE POUR LE TRAITEMENT DU CANCER
  申请人：ASTRAZENECA AB

  公开号：WO2017046216A1

  公开（公告）日：2017-03-23

  The specification generally relates to compounds of Formula (I): and pharmaceutically acceptable salts thereof, where Rl, R2, R3, R4 and R5 have any of the meanings defined herein. The specification also discloses the use of compounds of Formula (I) and salts thereof to treat or prevent ATM mediated disease, including cancer. The specification further relates to pharmaceutical compositions comprising substituted imidazo[4,5-c]quinolin-2-one compounds and pharmaceutically acceptable salts thereof; kits comprising such compounds and salts; methods of manufacture of such compounds and salts; and intermediates useful in such manufacture.

  该规范通常涉及Formula (I)的化合物及其药用盐，其中R1、R2、R3、R4和R5具有本规范中定义的任何含义。该规范还披露了利用Formula (I)的化合物及其盐来治疗或预防ATM介导的疾病，包括癌症。该规范进一步涉及包含取代咪唑并[4,5-c]喹啉-2-酮化合物及其药用盐的药物组合物；包含这些化合物和盐的试剂盒；制造这些化合物和盐的方法；以及在这种制造中有用的中间体。