2-吗啉烟腈 | 59025-37-5

• 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-吗啉烟腈
• 英文名称: 2-morpholinonicotinonitrile
• 英文别名: 2-morpholin-4-ylpyridine-3-carbonitrile
• CAS: 59025-37-5
• 化学式: C₁₀H₁₁N₃O
• mdl: MFCD04113612
• 分子量: 189.217
• InChiKey: QCXHZQXRAOOEQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险标志：
  GHS06
• 危险性描述：
  H301
• 危险性防范说明：
  P301 + P310

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Morpholino-3-cyanopyridine
Synonyms: 2-Morpholinonicotinonitrile

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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: 2-Morpholino-3-cyanopyridine
CAS number: 59025-37-5

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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: C10H11N3O
Molecular weight: 189.2

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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.

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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：

  2-吗啉烟腈 在 氢气 作用下， 反应 18.0h， 生成 [2-(4-吗啉)-3-吡啶]甲胺
  参考文献：
  名称：

  [EN] PYRIDAZINE COMPOUNDS FOR INHIBITING Nav1.8
  [FR] COMPOSÉS PYRIDAZINEG POUR INHIBER NAV1.8

  摘要：

  本发明揭示了用于抑制NaV1.8的吡啶并化合物以及用于治疗与增加NaV1.8活性或表达相关的病况、疾病或障碍的方法。

  公开号：

  WO2020014243A1
• 作为产物：
  描述：

  吗啉-4-基苯甲酸酯 、 3-氰基吡啶 在 Zn(TMP)₂ 、 copper diacetate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.0h， 以81%的产率得到2-吗啉烟腈
  参考文献：
  名称：

  铜催化 C?H 锌化杂芳烃和芳烃的亲电胺化

  摘要：

  杂芳烃和芳烃的直接胺化已经在一锅C - H锌化/铜催化的亲电胺化过程中实现。这种胺化方法提供了一种高效、快速的方法来获得各种杂芳胺和芳香胺，包括以前使用 C - H 胺化方法无法获得的胺。温和的反应条件和良好的官能团相容性证明了其在合成重要且复杂的胺类方面的巨大潜力。

  DOI：

  10.1002/anie.201311029

文献信息

• Transition metal-free amination of aryl halides—A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1016/j.tet.2008.11.072

  日期：2009.2

  intermediates is not necessary, allowing the synthesis of pyridine-2,6-diamines in ‘one-pot’. However, catalysts are in many cases not required to efficiently and selectively couple aryl halides with amines, making transition metal-free versions of the Buchwald–Hartwig reaction extremely attractive for the synthesis of N-arylated amines with substrates containing substituents on the aryl halide, which either promote

  提出了一种简单，可靠的反应方案，用于在无过渡金属的反应条件下，由芳基卤化物与各种（也是位阻的）胺反应衍生而来的各种N-芳基化胺的清洁，快速和高产率合成。二恶烷和KN（Si（CH 3）3）2被发现是该转化的理想溶剂和基础。观察到的转化率和产率极好，并且在大多数反应中进行的反应明显高于其催化形式的反应。此外，几乎可以选择性合成6-卤代吡啶-2-胺和不对称吡啶-2,6-二胺（分别来自2,6-二溴吡啶和2,6-二氯吡啶的连续反应）。在非常短的反应时间内即可获得定量收率（相对于2,6-二卤代吡啶）。不需要纯化6-卤代吡啶-2-胺中间体，从而可以在“一锅法”中合成吡啶-2,6-二胺。但是，催化剂在许多情况下不是有效地和选择性地使芳基卤化物与胺偶联，使无过渡金属形式的Buchwald-Hartwig反应对于合成N-芳基化胺（在芳基卤化物上具有取代基的底物）极具吸引力，这会促进区域选择性和/或不需要区域选择性胺化。
• Nicotinamide derivative or salt thereof
  申请人：Fujiwara Hideyasu

  公开号：US08772320B2

  公开（公告）日：2014-07-08

  An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. The present invention provides a nicotinamide derivative represented by the following formula (I) (wherein R1 represents a halogen atom; R2 represents a C1-12 alkyl group, a C2-12 alkenyl group, a C2-12 alkynyl group, a C3-8 cycloalkyl group, an aryl group, an ar-C1-6 alkyl group or a heterocyclic group, each optionally having at least one substituent; R3 represents an aryl group or a heterocyclic group each optionally having at least one substituent; and R4 and R5 each independently represent a hydrogen atom; and R2 and R4 may form a cyclic amino group optionally having at least one substituent together with the nitrogen atom to which they bind) or a salt thereof, and a pharmaceutical composition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.

  本发明的目的是提供一种具有优异Syk抑制活性的化合物和药物组合物。本发明提供了以下式子（I）所表示的烟酰胺衍生物（其中R1表示卤素原子；R2表示C1-12烷基、C2-12烯基、C2-12炔基、C3-8环烷基、芳基、芳基-C1-6烷基或杂环基，每个都可以选择性地具有至少一个取代基；R3表示芳基或杂环基，每个都可以选择性地具有至少一个取代基；R4和R5各自独立地表示氢原子；且R2和R4可以与它们结合的氮原子一起选择性地形成一个带有至少一个取代基的环状氨基团）或其盐，以及用于治疗Syk相关疾病的药物组合物，其包括该烟酰胺衍生物或其盐。
• NOVEL NICOTINAMIDE DERIVATIVE OR SALT THEREOF
  申请人：FUJIWARA Hideyasu

  公开号：US20130116430A1

  公开（公告）日：2013-05-09

  An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. The present invention provides a nicotinamide derivative represented by the following formula (I) (wherein R 1 represents a halogen atom; R 2 represents a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a C 3-8 cycloalkyl group, an aryl group, an ar-C 1-6 alkyl group or a heterocyclic group, each optionally having at least one substituent; R 3 represents an aryl group or a heterocyclic group each optionally having at least one substituent; and R 4 and R 5 each independently represent a hydrogen atom; and R 2 and R 4 may form a cyclic amino group optionally having at least one substituent together with the nitrogen atom to which they bind) or a salt thereof, and a pharmaceutical composition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.

  本发明的目的是提供一种具有优异的Syk抑制活性的化合物和制药组合物。本发明提供了一种由以下式(I)表示的烟酰胺衍生物（其中R1表示卤素原子；R2表示C1-12烷基、C2-12烯基、C2-12炔基、C3-8环烷基、芳基、芳基-C1-6烷基或杂环基，每种均可选地具有至少一个取代基；R3表示芳基或杂环基，每种均可选地具有至少一个取代基；R4和R5各自独立地表示氢原子；且R2和R4可以与它们结合的氮原子一起形成具有至少一个取代基的环状氨基团）或其盐，并且用于治疗Syk相关疾病的制药组合物包括该烟酰胺衍生物或其盐。
• Direct C(3)5−H Polyfluoroarylation of 2‐Amino/alkoxy Pyridines Enabled by a Transient and Electron‐deficient Palladium Intermediate
  作者：Animesh Das、Biplab Maji

  DOI：10.1002/chem.202301436

  日期：2023.7.20

  Herein, we present an unprecedented azine‐limited C5−H polyfluoroarylation of 2‐aminopyridines enabled by a transient and electron‐deficient perfluoroaryl‐Pd species via C−H/C−H coupling. The protocol further allows C3(5)−H polyfluoroarylation of 2‐alkoxypyridines guided by sterics and electronics for the first time. The late‐stage C−H functionalization of drugs, drug derivatives, and natural product derivatives and synthesis of C5‐aryl drug derivatives further demonstrated the method's utility. The preliminary mechanistic studies reveal that the synergistic combination of the bulky yet electrophilic perfluoroaryl‐Pd species and the partial nucleophilicity of the C5‐position of 2‐amino/alkoxy‐pyridines is the origin of reactivity and selectivity. Importantly, the first experimental evidence for the role of diisopropyl sulfide is provided.

  摘要在本文中，我们介绍了一种前所未有的偶氮限制的 2- 氨基吡啶的 C5-H 多氟芳基化反应，该反应通过 C-H/C-H 偶联由瞬时缺电子的全氟化芳基钯物种实现。该方案还首次实现了立体学和电子学指导下的 2-烷氧基吡啶的 C3(5)-H 多氟芳基化。药物、药物衍生物和天然产物衍生物的后期 C-H 功能化以及 C5 芳基药物衍生物的合成进一步证明了该方法的实用性。初步机理研究表明，笨重但亲电的全氟芳基钯物种与 2-氨基/烷氧基吡啶的 C5 位部分亲核性的协同组合是反应性和选择性的源泉。重要的是，实验首次证明了二异丙基硫醚的作用。
• Synthesis, Crystal Structure, Spectroscopic Characterization, in Vitro and in Silico Studies of Water-Soluble (Z)-N'-Hydroxy-2-Morpholinonicotinimidamide
  作者：S. Geetha、R. Sribalan、S. Lakshmi

  DOI：10.1134/s0022476624040103

  日期：2024.4

  Abstract A water-soluble compound (Z)-N′-hydroxy-2-morpholinonicotinimidamide was synthesized, and it has a multi-functional group, such as morpholine, pyridine, and oxime. The synthesized compound was characterized by various spectroscopic techniques such as NMR, FTIR, UV-Visible, elemental analysis, and single-crystal XRD. The molecule was investigated using computational methods, such as DFT and

  抽象的 合成了一种具有吗啉、吡啶、肟等多功能基团的水溶性化合物(Z)-N'-羟基-2-吗啉烟酰亚胺。通过核磁共振、傅立叶变换红外光谱、紫外-可见光、元素分析和单晶 XRD 等多种光谱技术对合成的化合物进行了表征。使用 DFT 和 MEP 等计算方法对分子进行研究，以确定分子表面的电子特征。在这些研究的帮助下，还用糖尿病和炎症相关酶进行了对接实验。结果与遵循蛋白质抑制方法的体外抗糖尿病和抗炎研究相匹配。所获得的结果强烈表明，鉴于该化合物可以在溶解度方面支持生物系统，因此可以对该化合物进行更好的体内活性研究。