2-氨基-4-氯-5-溴吡啶 | 942947-94-6

• 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 - 吡啶及其衍生物
• 中文名称: 2-氨基-4-氯-5-溴吡啶
• 中文别名: 2-氨基-5-溴-4-氯吡啶
• 英文名称: 5-bromo-4-chloropyridin-2-amine
• 英文别名: 2-amino-5-bromo-4-chloropyridine；5-bromo-4-chloro-2-aminopyridine
• CAS: 942947-94-6
• 化学式: C₅H₄BrClN₂
• mdl: MFCD12407282
• 分子量: 207.457
• InChiKey: DDOFUMWLNSICHU-UHFFFAOYSA-N

物化性质

• 沸点：
  271.6±35.0 °C(Predicted)
• 密度：
  1.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-4-chloropyridin-2-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-4-chloropyridin-2-amine
CAS number: 942947-94-6

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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: C5H4BrClN2
Molecular weight: 207.5

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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

2-氨基-4-氯-5-溴吡啶可用于合成2,4-二氯-5-溴吡啶。后者是重要的生物医药中间体，广泛应用于各种药物的合成中。由于其分子量小、结构独特，可以衍生出多种下游产品，因此具有广泛的用途。

反应信息

• 作为反应物：
  描述：

  2-氨基-4-氯-5-溴吡啶 在 copper(l) iodide 、 四(三苯基膦)钯 、 三甲基氯硅烷 、 甲烷磺酸 、 硫酸 、 potassium tert-butylate 、 水 、 碘 、 异丙基氯化镁 、 sodium hydride 、 高碘酸 、 二异丙胺 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 74.75h， 生成 培米加替尼
  参考文献：
  名称：

  DERIVATIVES OF AN FGFR INHIBITOR

  摘要：

  本公开涉及一种成纤维细胞生长因子受体（FGFR）抑制剂的衍生物（例如，羟基，酮基，葡萄糖醛酸盐，磺酸盐和氘代物），包括其制备方法以及在制备过程中有用的中间体，这些衍生物在治疗FGFR介导的疾病如癌症方面是有用的。

  公开号：

  US20210171522A1
• 作为产物：
  描述：

  2-氨基-4-氯吡啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以89%的产率得到2-氨基-4-氯-5-溴吡啶
  参考文献：
  名称：

  新型吡啶酮衍生物的设计、合成和评估作为潜在治疗前列腺癌的有效 BRD4 抑制剂

  摘要：

  由于雄激素受体 (AR) 可以与 BRD4 蛋白结合，并且这种结合可以被 BRD4 抑制剂阻断，因此靶向 BRD4 已成为治疗前列腺癌 (PC) 的一种有前途的方法。在此，我们设计并合成了一系列 5-(1-benzyl-1 H -indazol-6-yl)-4-ethoxy-1-methylpyridin-2(1 H )-one 衍生物作为前列腺癌的新型 BRD4 抑制剂。其中，化合物13表现出最强的 BRD4 抑制活性，IC 50值为 18 nM。此外，13对恩杂鲁胺耐药的 22RV1 细胞显示出有效的抗增殖活性。作用机制研究表明，13通过调节 Bcl-2/Bax 蛋白和激活 caspase-3 信号通路诱导细胞凋亡。此外，在蛋白质印迹分析中，22RV1 细胞中的 c-Myc 水平显着降低。这些发现共同表明化合物13可能用于治疗前列腺癌。

  DOI：

  10.1016/j.bioorg.2021.105575

文献信息

• [EN] ARYL ETHER-BASE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES DE TYPE ARYLÉTHER-BASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015038112A1

  公开（公告）日：2015-03-19

  The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

  本公开涉及一般可抑制AAK1（适配器相关激酶1）的化合物，包括这些化合物的组合物，以及抑制AAK1的方法。
• Discovery of Potent, Selective, and Orally Bioavailable Small-Molecule Modulators of the Mediator Complex-Associated Kinases CDK8 and CDK19
  作者：Aurélie Mallinger、Kai Schiemann、Christian Rink、Frank Stieber、Michel Calderini、Simon Crumpler、Mark Stubbs、Olajumoke Adeniji-Popoola、Oliver Poeschke、Michael Busch、Paul Czodrowski、Djordje Musil、Daniel Schwarz、Maria-Jesus Ortiz-Ruiz、Richard Schneider、Ching Thai、Melanie Valenti、Alexis de Haven Brandon、Rosemary Burke、Paul Workman、Trevor Dale、Dirk Wienke、Paul A. Clarke、Christina Esdar、Florence I. Raynaud、Suzanne A. Eccles、Felix Rohdich、Julian Blagg

  DOI：10.1021/acs.jmedchem.5b01685

  日期：2016.2.11

  complex-associated cyclin-dependent kinase CDK8 has been implicated in human disease, particularly in colorectal cancer where it has been reported as a putative oncogene. Here we report the discovery of 109 (CCT251921), a potent, selective, and orally bioavailable inhibitor of CDK8 with equipotent affinity for CDK19. We describe a structure-based design approach leading to the discovery of a 3,4,5-trisubstituted-2-aminopyridine

  介体复合物相关的细胞周期蛋白依赖性激酶 CDK8 与人类疾病有关，特别是在结肠直肠癌中，据报道它是一种推定的癌基因。在这里，我们报告了109 (CCT251921) 的发现，它是一种有效的、选择性的和口服生物可利用的 CDK8 抑制剂，对 CDK19 具有等效的亲和力。我们描述了一种基于结构的设计方法，导致发现了 3,4,5-三取代-2-氨基吡啶系列，并介绍了物理化学性质分析的应用，以成功降低体内代谢清除率，最大限度地减少转运蛋白介导的胆汁消除，同时保持可接受的水溶性。化合物109提供了体外生化、药代动力学和物理化学性质的最佳折衷，并适用于发展为癌症动物模型。
• [EN] TAM KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES TAM
  申请人：SYROS PHARMACEUTICALS INC

  公开号：WO2018191587A1

  公开（公告）日：2018-10-18

  Described herein are compounds, methods of making such compounds, compositions (e.g., pharmaceutical compositions/medicaments) that include such compounds, and methods of using such compounds to treat diseases, such as cancer.

  本文描述了化合物，制备这种化合物的方法，包括这种化合物的组合物（例如，包含这种化合物的药物组合物/药物），以及使用这种化合物治疗疾病（如癌症）的方法。
• [EN] NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF DISEASES<br/>[FR] NOUVEAUX COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES ASSOCIÉES POUR LE TRAITEMENT DE MALADIES
  申请人：GALAPAGOS NV

  公开号：WO2020239658A1

  公开（公告）日：2020-12-03

  The present invention discloses compounds according to Formula (I), wherein R1a, R1b, R1c, R2a, W1, W2, X1, X2, X3, Y, and Z are as defined herein. The present invention relates to compounds, methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of inflammatory diseases, autoinflammatory diseases, autoimmune diseases, proliferative diseases, fibrotic diseases, transplantation rejection, diseases involving impairment of cartilage turnover, congenital cartilage malformation, diseases involving impairment of bone turnover, diseases associated with hypersecretion of IL-6, diseases associated with hypersecretion of TNFα, interferons, IL-12 and/or IL-23, respiratory diseases, endocrine and/or metabolic diseases, cardiovascular diseases, dermatological diseases, and/or abnormal angiogenesis associated diseases by administering the compound of the invention.

  本发明公开了根据式（I）的化合物，其中R1a、R1b、R1c、R2a、W1、W2、X1、X2、X3、Y和Z如本文所定义。本发明涉及化合物、其生产方法、包括其在内的制药组合物，以及使用这些化合物进行预防和/或治疗炎症性疾病、自身炎症性疾病、自身免疫性疾病、增生性疾病、纤维化疾病、移植排斥、涉及软骨周转障碍的疾病、先天软骨畸形、涉及骨周转障碍的疾病、与IL-6过度分泌有关的疾病、与TNFα、干扰素、IL-12和/或IL-23过度分泌有关的疾病、呼吸系统疾病、内分泌和/或代谢性疾病、心血管疾病、皮肤病和/或异常血管生成相关疾病的治疗方法，通过给予本发明的化合物。
• Synthesis and evaluation of the anticoccidial activity of trifluoropyrido[1,2-a]pyrimidin-2-one derivatives
  作者：Laurence Silpa、Alisson Niepceron、Fabrice Laurent、Fabien Brossier、Mélanie Pénichon、Cécile Enguehard-Gueiffier、Mohamed Abarbri、Anne Silvestre、Julien Petrignet

  DOI：10.1016/j.bmcl.2015.11.018

  日期：2016.1

  of our chemical library to discover new molecules exhibiting in vitro activity against the invasion of host cells by Eimeria tenella revealed a lead compound with an IC50 of 15μM. Structure-activity relationship studies were conducted with 34 newly synthesized compounds to identify more active molecules and enhance in vitro activity against the parasite. Four compounds were more effective in inhibiting

  筛选我们的化学文库以发现表现出抗艾美尔球虫侵袭宿主细胞的体外活性的新分子，发现了一种铅化合物，IC50为15μM。使用34种新合成的化合物进行了结构-活性关系研究，以鉴定更多活性分子并增强体外抗寄生虫活性。四种化合物在体外抑制MDBK细胞入侵方面比先导化合物更有效。