5-氯-2-甲氧基烟酸 | 54916-65-3

• 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-氯-2-甲氧基烟酸
• 英文名称: 5-chloro-2-methoxynicotinic acid
• 英文别名: 5-chloro-2-methoxypyridine-3-carboxylic acid
• CAS: 54916-65-3
• 化学式: C₇H₆ClNO₃
• mdl: MFCD08236790
• 分子量: 187.583
• InChiKey: DPIJNAABZCWXFD-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148°
• 沸点：
  301.3±37.0 °C(Predicted)
• 密度：
  1.43

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloro-2-methoxynicotinic acid
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-Chloro-2-methoxynicotinic acid
CAS number: 54916-65-3

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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: C7H6ClNO3
Molecular weight: 187.6

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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.

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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

反应信息

• 作为反应物：
  描述：

  5-氯-2-甲氧基烟酸 在 diisopropyl aluminum hydride 、 硫酸 、 氢溴酸 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 7.25h， 生成 6-chloro-2,3-dihydro-2-methyl-4H-pyrano<2,3-b>pyridin-4-one
  参考文献：
  名称：

  螺旋乙内酰脲醛糖还原酶抑制剂衍生自8-Aza-4-chromanones。

  摘要：

  制备了一系列衍生自8-氮杂苯并二氢吡喃酮（2,3-二氢-4H-吡喃并[2,3-b]吡啶-4-酮的螺旋乙内酰脲）的醛糖还原酶抑制活性。必须对Bucherer-Bergs标准条件进行彻底修改，以将收率从不到1％提高到可接受的50％范围。最有效的化合物之一是cis-6'-chloro-2'，3'-dihydro-2'-methylspiro [imidazolidine-4,4'-4'H-pyrano [2,3-b] pyridine] -2 ，5-二酮; 该化合物的拆分结果表明2'R，4'S对映异构体16是该系列中活性最高的螺乙内酰脲，对人胎盘醛糖还原酶的IC50为7.5 x 10（-9）。

  DOI：

  10.1021/jm00169a005
• 作为产物：
  描述：

  2-甲氧基烟酸 在 sodium hypochlorite 作用下， 以75%的产率得到5-氯-2-甲氧基烟酸
  参考文献：
  名称：

  螺旋乙内酰脲醛糖还原酶抑制剂衍生自8-Aza-4-chromanones。

  摘要：

  制备了一系列衍生自8-氮杂苯并二氢吡喃酮（2,3-二氢-4H-吡喃并[2,3-b]吡啶-4-酮的螺旋乙内酰脲）的醛糖还原酶抑制活性。必须对Bucherer-Bergs标准条件进行彻底修改，以将收率从不到1％提高到可接受的50％范围。最有效的化合物之一是cis-6'-chloro-2'，3'-dihydro-2'-methylspiro [imidazolidine-4,4'-4'H-pyrano [2,3-b] pyridine] -2 ，5-二酮; 该化合物的拆分结果表明2'R，4'S对映异构体16是该系列中活性最高的螺乙内酰脲，对人胎盘醛糖还原酶的IC50为7.5 x 10（-9）。

  DOI：

  10.1021/jm00169a005

文献信息

• [EN] GCN2 MODULATOR COMPOUNDS<br/>[FR] COMPOSÉS MODULATEURS DE GCN2
  申请人：BLACK BELT TX LTD

  公开号：WO2021165346A1

  公开（公告）日：2021-08-26

  The disclosures herein relate to novel compounds of Formula (1): or a salt thereof, wherein X, Y, R1, R2, R3, R4 and R5 are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with General Control Nondepressible 2 (GCN2).

  本公开涉及式（1）的新化合物或其盐，其中X、Y、R1、R2、R3、R4和R5如本文所定义，并其在治疗、预防、改善、控制或减少与广泛控制不可抑制2（GCN2）相关的疾病风险中的用途。
• Azolidinedione derivatives
  申请人：Pfizer Inc.

  公开号：US04980357A1

  公开（公告）日：1990-12-25

  A series of novel spiro-deteroazolones derived from a 2,3-dihydropryrano[2,3-b]pyridine ring system have been prepared, including their pharmaceutically acceptable salts. These compounds are useful in therapy as aldose reductase inhibitors for the control of certain chronic diabetic complications. Typical member compounds include spiro-imides, spiro-oxazolidinediones, spiro-thiazolidinediones and spiro-imidazolidinediones derived from the aforesaid ring system. (4'S) (2'R)-6'-Chloro-2',3'-dihydro-2'-methyl-spiro-[imidazolidine-4,4'-4'H-pyra no[2,3-b]pyridine]-2,5-dione represents a typical and preferred member compound. Methods for preparing all these compounds from known starting materials are provided.

  一系列源自2,3-二氢吡喃并[2,3-b]吡啶环系统的新型螺二氮杂环酮已被制备，包括其药学上可接受的盐。这些化合物在治疗上作为醛糖还原酶抑制剂，用于控制某些慢性糖尿病并发症是有用的。典型的成员化合物包括源自上述环系统的螺酰亚胺、螺噁唑烷二酮、螺噻唑烷二酮和螺咪唑烷二酮。(4'S)(2'R)-6'-氯-2',3'-二氢-2'-甲基-螺[咪唑烷-4,4'-4'H-吡喃并[2,3-b]吡啶]-2,5-二酮代表了一个典型且优选的成员化合物。提供了从已知起始原料制备所有这些化合物的方法。
• Chlorination of 2-methoxynicotinic acid
  申请人：Pfizer Inc.

  公开号：US04716231A1

  公开（公告）日：1987-12-29

  A novel process for chlorinating 2-methoxynicotinic acid at the 5-position of the molecule is disclosed. The process involves the use of an alkali metal hypochlorite as the chlorinating agent in a homogeneous aqueous solvent system. The compound so produced, 5-chloro-2-methoxynicotinic acid, is known to be useful as an intermediate leading to various oral hypoglycemic agents of the benzenesulfonylurea class.

  揭示了一种在分子的5位位置氯化2-甲氧基烟酸的新工艺。该工艺涉及在均相水溶剂体系中使用碱金属次氯酸盐作为氯化剂。所生产的化合物，5-氯-2-甲氧基烟酸，已知可作为通向苯磺酰脲类口服降糖剂的各种中间体。
• Development of novel conformationally restricted selective Clk1/4 inhibitors through creating an intramolecular hydrogen bond involving an imide linker
  作者：Dalia S. El-Gamil、Ahmed K. ElHady、Po-Jen Chen、Tsong-Long Hwang、Ashraf H. Abadi、Mohammad Abdel-Halim、Matthias Engel

  DOI：10.1016/j.ejmech.2022.114411

  日期：2022.8

  novel series of N-aroylated 5-methoxybenzothiophene-2-carboxamides (imides) as potent and selective Clk1/4 inhibitors. Potency of this series was found to be mainly dependent on the presence of an intramolecular H-bond between an ortho-methoxy group and the imide NH, that stabilizes a nearly coplanar conformation of high affinity to the ATP binding pocket(s) of Clk1/4. The two most potent hits in this

  作为前 mRNA 可变剪接的主要调节因子，发现不同的 Clk 同种型在各种肿瘤类型中过度表达，并且最近作为癌症治疗的潜在靶标受到了广泛关注。几项研究报告了有效的小分子 Clk1/4 抑制剂，具有良好的细胞抗癌活性；然而，它们的临床应用通常受到其对脱靶（主要是 Clk2 和 Dyrk1A）的选择性受损的阻碍。在这项研究中，我们提出了一系列新的N-芳酰化 5-甲氧基苯并噻吩-2-羧酰胺 (酰亚胺) 作为有效和选择性的 Clk1/4 抑制剂。发现该系列的效力主要取决于邻位之间存在分子内氢键-甲氧基和亚胺 NH，可稳定对 Clk1/4 的 ATP 结合口袋具有高亲和力的几乎共面的构象。该系列中最有效的两个产品，化合物20（4-氟-2-甲氧基）和31（5-氯-2-甲氧基）的无细胞 Clk1 IC 50分别为 4 和 9.7 nM，此外还具有前所未有的选择性与 Clk2 相比，对 Clk1 的亲和力分别高
• Benzenesulfonylurea derivatives
  申请人：Pfizer Inc.

  公开号：US03961065A1

  公开（公告）日：1976-06-01

  Certain novel benzenesulfonylurea compounds derived from a nitrogen-containing carboxylic acid have been prepared by reacting an appropriate sulfonamide with an organic isocyanate or a tri-substituted urea equivalent thereof. The sulfonylureas so obtained are useful in therapy as oral hypoglycemic agents. Typical members include those compounds derived from 2-methoxy-nicotinic acid, of which 1-cyclohexyl-3-4-[2-(5-bromo-2-methoxynicotinamido)ethyl]benzenesulfonyl} urea is a most preferred embodiment.

  某些新型苯磺酰脲化合物是由含氮羧酸与适当的磺酰胺经有机异氰酸酯或三取代脲等当量反应制备而成。所得的磺酰脲类化合物可用作口服降血糖药物。典型的成员包括从2-甲氧基烟酸酸衍生的化合物，其中1-环己基-3-4-[2-(5-溴-2-甲氧基烟酰胺基)乙基]苯磺酰}脲是最优选的实施形式。