N-甲氧基-n-甲基-1H-吲唑-3-羧酰胺 | 351457-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: N-甲氧基-n-甲基-1H-吲唑-3-羧酰胺
• 中文别名: N-甲氧基-N-甲基-1H-吲唑-3-羧酰胺
• 英文名称: N-methoxy-N-methyl-1H-indazole-3-carboxamide
• CAS: 351457-12-0
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: NRQALXRUZKPBKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Methoxy-N-methyl-1H-indazole-3-carboxamide
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: N-Methoxy-N-methyl-1H-indazole-3-carboxamide
CAS number: 351457-12-0

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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: C10H11N3O2
Molecular weight: 205.2

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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：

  N-甲氧基-n-甲基-1H-吲唑-3-羧酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以76%的产率得到3-醛基吲唑
  参考文献：
  名称：

  通过Wittig-Horner反应获得2-氮杂色氨酸和脱氢衍生物的新实用途径

  摘要：

  受保护的3-甲酰基吲唑1与（±）-N-（苄氧羰基）-α-膦酰基甘氨酸三甲酯2的Wittig-Horner反应已被开发为脱氢2-氮杂色氨酸和氨基酸衍生物的新型实用合成方法。讨论了5-溴-3-甲酰基吲唑的制备。

  DOI：

  10.1016/j.tetlet.2007.02.042
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 吡啶 、 硫酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 49.5h， 生成 N-甲氧基-n-甲基-1H-吲唑-3-羧酰胺
  参考文献：
  名称：

  吲唑类化合物及其制备方法和应用

  摘要：

  本发明提供一种吲唑类化合物及制备方法和应用。本发明以吲唑作为结构母核，设计并合成了一系列全新的小分子PI3Kδ抑制剂，并对该类化合物进行了PI3Kδ激酶抑制活性测试和MV‑4‑11细胞活性测试，本发明提供的吲唑类化合物表现出更好的激酶亚型选择性，并且对肿瘤细胞株表现出了更好的体外增殖抑制活性。可在制备抗肿瘤药物以及在制备抑制PI3Kδ激酶的活性药物中的应用，为抗肿瘤药物研究提供了新的途径。本发明原料廉价易得、制备方法简单、适合大规模生产。结构通式如下：

  公开号：

  CN110156785B

文献信息

• POLYSUBSTITUTED DERIVATIVES OF 6-HETEROARYLIMIDAZO[1,2-a]PYRIDINES, AND PREPARATION AND THERAPEUTIC USE THEREOF
  申请人：DE PERETTI Danielle

  公开号：US20110065700A1

  公开（公告）日：2011-03-17

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , Het and X are as defined in the disclosure, or an acid addition salt thereof, and the therapeutic use and process of synthesis thereof.

  式(I)的化合物： 其中R1、R2、R3、R4、Het和X如披露中所定义，或其酸盐加合物，以及其治疗用途和合成过程。
• [EN] BICYCLIC HETEROARYL INDOLE ANALOGUES USEFUL AS ROR GAMMA MODULATORS<br/>[FR] ANALOGUES DE L'INDOLE HÉTEROARYLE BICYCLIQUE UTILES EN TANT QUE MODULATEURS DE GAMMA ROR
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2015087234A1

  公开（公告）日：2015-06-18

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein X, X1, M, R2, R3, R4, R5, m, n, and p are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORγt). These compounds prevent, inhibit, or suppress the action of RORγt and are therefore useful in the treatment of RORγt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, neurodegenerative diseases and cancer.

  本公开涉及式(I)的化合物及其药用盐，其中X、X1、M、R2、R3、R4、R5、m、n和p如本文所定义，这些化合物作为视黄醇相关孤儿受体γt（RORγt）调节剂具有活性。这些化合物可以预防、抑制或抑制RORγt的作用，因此在治疗RORγt介导的疾病、疾病、综合症或病况中具有用处，例如疼痛、炎症、慢性阻塞性肺病（COPD）、哮喘、类风湿关节炎、结肠炎、多发性硬化症、神经退行性疾病和癌症。
• [EN] P2X3 AND/OR P2X2/3 COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS P2X3 ET/OU P2X2/3 ET MÉTHODES ASSOCIÉES
  申请人：ASANA BIOSCIENCES LLC

  公开号：WO2018064135A1

  公开（公告）日：2018-04-05

  The present disclosure provides novel compounds and methods for preparing and using these compounds. In one embodiment, the compounds are of the structure of formula (I), wherein R1-R7 are defined herein. In a further embodiment, these compounds are useful in method for regulating one or both of the P2X3 or P2X2/3 receptors. In another embodiment, these compounds are useful for treating pain in patients by administering one or more of the compounds to a patient. In another embodiment, these compounds are useful for treating respiratory dysfunction in patients by administering one or more of the compounds to a patient.

  本公开提供了新颖的化合物和制备和使用这些化合物的方法。在一种实施例中，这些化合物具有如下式（I）的结构，其中R1-R7在此处定义。在另一种实施例中，这些化合物在调节P2X3或P2X2/3受体中的一种或两种的方法中是有用的。在另一种实施例中，通过向患者施用一种或多种化合物来治疗患者的疼痛是有用的。在另一种实施例中，通过向患者施用一种或多种化合物来治疗患者的呼吸功能障碍是有用的。
• Design and synthesis of a new indazole library: direct conversion of N-methoxy-N-methylamides (Weinreb amides) to 3-keto and 3-formylindazoles
  作者：François Crestey、Silvia Stiebing、Rémi Legay、Valérie Collot、Sylvain Rault

  DOI：10.1016/j.tet.2006.10.063

  日期：2007.1

  Grignard or lithiated reagents on the new Weinreb amides 3 and 4 afforded efficiently the corresponding ketones and allowed the design and synthesis of a new indazole library. These 3-ketoindazoles were obtained by a direct and original conversion of N-methoxy-N-methylamides with good yields. Furthermore, the reduction of 3 with LiAlH4 furnished the corresponding aldehydes as a versatile and efficient pathway

  在新的Weinreb酰胺3和4上亲核添加格氏试剂或锂化试剂可有效提供相应的酮，并允许设计和合成新的吲唑文库。这些3-酮吲唑是通过N-甲氧基-N-甲基酰胺的直接和原始转化以良好的收率获得的。此外，用LiAlH 4还原3可以提供相应的醛，作为通向3-甲酰基吲唑的一种通用而有效的途径。
• [EN] INDAZOLE-3-CARBOXAMIDES AND THEIR USE AS WNT/B-CATENIN SIGNALING PATHWAY INHIBITORS<br/>[FR] INDAZOLE-3-CARBOXAMIDES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA VOIE DE SIGNALISATION PAR WNT/Beta-CATÉNINE
  申请人：SAMUMED LLC

  公开号：WO2013040215A1

  公开（公告）日：2013-03-21

  lndazole-3-carboxamide compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of an indazole-3- carboxamide compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

  本文披露了用于治疗各种疾病和病理的吲唑-3-羧酰胺化合物。更具体地，本文涉及使用吲唑-3-羧酰胺化合物或其类似物治疗由Wnt途径信号激活所特征的疾病（例如癌症、异常细胞增殖、血管生成和骨关节炎），调节由Wnt途径信号介导的细胞事件，以及由于Wnt途径和/或Wnt信号组分之一或多个的突变或失调而引起的遗传疾病和神经系统疾病/紊乱/疾病。还提供了治疗与Wnt相关疾病状态的方法。