5-溴-2-羟基异烟酸甲酯 | 913836-17-6

• 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-2-羟基异烟酸甲酯
• 中文别名: 2-羟基-5-溴异烟酸甲酯
• 英文名称: methyl 5-bromo-2-oxo-1,2-dihydropyridine-4-carboxylate
• 英文别名: Methyl 5-bromo-2-hydroxyisonicotinate；methyl 5-bromo-2-oxo-1H-pyridine-4-carboxylate
• CAS: 913836-17-6
• 化学式: C₇H₆BrNO₃
• 分子量: 232.034
• InChiKey: XOMMLGBSSAVOET-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±42.0 °C(Predicted)
• 密度：
  1.737±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 5-bromo-2-hydroxyisonicotinate
Synonyms: Methyl 5-Bromo-2-hydroxy-4-pyridinecarboxylate; 5-Bromo-4-methoxycarbonyl-2(1H)-pyridinone

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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: Methyl 5-bromo-2-hydroxyisonicotinate
CAS number: 913836-17-6

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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: C7H6BrNO3
Molecular weight: 232.0

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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

5-溴-2-羟基异烟酸甲酯是一种羧酸酯类衍生物，主要用于医药中间体的合成。

制备时，在装有机械搅拌装置和回流冷凝管的三口烧瓶中加入80 mL甲醇及5-溴-2-羟基异烟酸。室温下缓慢滴加1.0 mL浓硫酸，滴加完毕后进行回流反应30小时（通过薄层色谱跟踪监测）。反应完成后，浓缩至约30 mL，然后倒入60 mL水中。使用20 mL乙醚萃取两次，乙醚层用5%碳酸钠溶液洗涤一次，并用水洗至中性，再用无水硫酸镁干燥后蒸去乙醚，最终得到5-溴-2-羟基异烟酸甲酯。

反应信息

• 作为反应物：
  描述：

  5-溴-2-羟基异烟酸甲酯 在 三乙基硅烷 、 四(三苯基膦)钯 、 氨 、 palladium diacetate 、 sodium carbonate 、 caesium carbonate 、 三乙胺 、 silver carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 132.0h， 生成 5-(1-methyl-1H-pyrazol-4-yl)-2,6-naphthyridin-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  [EN] INHIBITOR COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS

  摘要：

  本发明涉及式(I)的化合物，其中R、R、Ar、W、X和Z均如本文所定义。本发明的化合物已知可以通过直接或间接地与Mps1激酶本身相互作用来抑制单丝粒体1（Mps1，也称为TTK）激酶的纺锤体检查点功能。具体而言，本发明涉及将这些化合物用作治疗和/或预防增殖性疾病，如癌症的治疗剂。本发明还涉及制备这些化合物的方法，以及包含它们的药物组合物。

  公开号：

  WO2014037750A1
• 作为产物：
  描述：

  5-溴-2-甲氧基异烟醛 在 甲酸 、 硫酸 、 氢溴酸 、 双氧水 作用下， 以 水 为溶剂， 生成 5-溴-2-羟基异烟酸甲酯
  参考文献：
  名称：

  ANTI-FIBROTIC PYRIDINONES

  摘要：

  揭示了吡啶酮化合物，制备这些化合物的方法，以及治疗纤维化疾病的方法。

  公开号：

  US20140094456A1

文献信息

• ARYL AND HETEROARYL FUSED LACTAMS
  申请人：PFIZER INC.

  公开号：US20140179667A1

  公开（公告）日：2014-06-26

  This invention relates to compounds of general formula (I) in which R 1 , R 2 , U, V, L, M, R 5 , m, X, Y and Z are as defined herein, and the pharmaceutically acceptable salts thereof, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer.

  本发明涉及具有通用公式（I）的化合物，其中R1，R2，U，V，L，M，R5，m，X，Y和Z定义如本文中所述，以及药用可接受的盐，包含此类化合物和盐的药物组合物，以及使用此类化合物、盐和组合物治疗异常细胞生长，包括癌症的方法。
• [EN] SPIROPIPERIDINE ALLOSTERIC MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] MODULATEURS ALLOSTÉRIQUES DE SPIROPIPÉRIDINE DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2019212927A1

  公开（公告）日：2019-11-07

  The present disclosure relates to compounds of formula I that are useful as modulators of 7 nAChR, compositions comprising such compounds, and the use of such compounds for preventing, treating, or ameliorating disease, particularly disorders of the central nervous system such as cognitive impairments in Alzheimer's disease, Parkinson's disease, and schizophrenia, as well as for L-DOPA induced-dyskinesia and inflammation (I).

  本公开涉及公式I的化合物，这些化合物可用作7 nAChR的调节剂，包含这些化合物的组合物，以及利用这些化合物预防、治疗或改善疾病，特别是中枢神经系统疾病，如阿尔茨海默病、帕金森病和精神分裂症中的认知障碍，以及L-多巴引起的运动障碍和炎症。
• NOVEL SUBSTITUTED BIARYL COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20190144433A1

  公开（公告）日：2019-05-16

  Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof: Also disclosed herein are uses of a compound disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of a composition in the potential treatment or prevention of an IDO-associated disease or disorder.

  本文披露了一种具有化学式（I）的化合物，或其药学上可接受的盐：本文还披露了本文披露的化合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。本文还披露了包含本文披露的化合物的组合物。本文还披露了组合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。
• [EN] HETEROCYCLIC WDR5 INHIBITORS AS ANTI-CANCER COMPOUNDS<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE WDR5 UTILISÉS EN TANT QUE COMPOSÉS ANTICANCÉREUX
  申请人：NOVARTIS AG

  公开号：WO2021028806A1

  公开（公告）日：2021-02-18

  The present invention provides compounds of Formula (I) or a pharmaceutically acceptable salt thereof; (I) which are inhibitors of WDR5. The present invention also provides pharmaceutical compositions comprising such compounds, compositions comprising such compounds with an additional therapeutic agent and the therapeutic uses of such compounds.

  本发明提供了式（I）的化合物或其药学上可接受的盐；（I）这些化合物是WDR5的抑制剂。本发明还提供了包含这些化合物的药物组合物，包含这些化合物与额外治疗剂的组合物以及这些化合物的治疗用途。
• [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS
  申请人：THE TRUSTEES OF PRINCETON UNIVERISTY

  公开号：WO2021151062A1

  公开（公告）日：2021-07-29

  Provided herein are novel heterocyclic compounds, for example, compounds having Formula I, I-P, II, lI-P, or III. Also provided herein are pharmaceutical compositions comprising the compounds and methods of using the same, for example, in inhibiting aldehyde dehydrogenases and/or for treating various cancers, cancer metastasis, type 2 diabetes, pulmonary arterial hypertension (PAH) or neointimal hyperplasia (NIH).

  本文提供了新颖的杂环化合物，例如具有I、I-P、II、II-P或III式的化合物。本文还提供了包含这些化合物的药物组合物以及使用这些组合物的方法，例如用于抑制醛脱氢酶和/或治疗各种癌症、癌症转移、2型糖尿病、肺动脉高压（PAH）或新生内膜增生（NIH）。