5-氨基-1-甲基-吡唑-4-甲腈 | 5334-41-8

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-甲基-吡唑-4-甲腈
• 中文别名: 1-甲基-4-氰基-5-氨基-1,2-吡唑；5-氨基-1-甲基-4-氰基吡唑
• 英文名称: 5-amino-4-cyano-1-methylpyrazole
• 英文别名: 5-Amino-1-methyl-1H-pyrazole-4-carbonitrile；5-amino-1-methylpyrazole-4-carbonitrile；5-Amino-1-methyl-pyrazol-4-carbonitril；1-methyl-4-cyano-5-aminopyrazole；5-amino-4-cyano-1-methyl-1H-pyrazole；1-Methyl-4-cyano-5-amino-pyrazol；5-Amino-4-cyan-1-methyl-pyrazol
• CAS: 5334-41-8
• 化学式: C₅H₆N₄
• mdl: MFCD00114569
• 分子量: 122.129
• InChiKey: MZFBWODPTSTYAI-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223°C
• 沸点：
  342.4±27.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933199090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331
• 储存条件：
  -20°C 冰箱

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Amino-1-methyl-1H-pyrazole-4-carbonitrile
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-Amino-1-methyl-1H-pyrazole-4-carbonitrile
CAS number: 5334-41-8

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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: C5H6N4
Molecular weight: 122.1

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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：

  5-氨基-1-甲基-吡唑-4-甲腈 在 盐酸 、 sodium nitrite 、 尿素 、 copper(l) chloride 作用下， 以 水 为溶剂， 以84%的产率得到5-氯-1-甲基-1H-吡唑-4-甲腈
  参考文献：
  名称：

  PROCESS OF PREPARATION OF AZIMSULFURON

  摘要：

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有式I的化合物， 在氯代溶剂（如二氯甲烷、1,2-二氯乙烷）中，通过在水杨酸或甲酸和氯气或次氯酸钠的存在下，用盐酸处理；或者在水环醚（如四氢呋喃、1,4-二噁烷）中，通过在水杨酸和N-氯琥珀酰亚胺或过氧化氢的存在下，用盐酸处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。

  公开号：

  US20150112063A1
• 作为产物：
  描述：

  4-cyano-5-<(methoxymethylene)amino>-1-methylpyrazole 在 三氟乙酸 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 72.0h， 生成 5-氨基-1-甲基-吡唑-4-甲腈
  参考文献：
  名称：

  Rearrangements in heterocyclic synthesis: a novel translocation of an (N-amino-N-methylamino)methylene group from a heterocyclic N-amino-N-methylformamidine side chain to the vinylogous nitrile function

  摘要：

  DOI：

  10.1021/jo00237a028

文献信息

• 一种四唑嘧磺隆关键中间体的制备方法及其 应用
  申请人：江西安利达化工有限公司

  公开号：CN105384725B

  公开（公告）日：2018-06-22

  本发明提供一种1‑甲基‑4‑(2‑甲基‑2H‑四氮唑‑5‑基)‑1H‑吡唑‑5‑磺酰胺的制备方法，包括以下步骤：以原甲酸三甲酯和丙二腈为起始原料，经过三步反应得到1‑甲基‑5‑氨基‑4‑(四氮唑‑5‑基)吡唑；然后在缚酸剂存在下，与硫酸二甲酯反应，得到2‑甲基‑5‑(1‑甲基‑5‑氨基‑1H‑吡唑‑4‑基)‑2H‑四氮唑；在酸性条件下，经亚硝酸钠重氮化，再与亚硫酸钠‑氯化铜‑乙酸混合物反应；最后经氨水解，得到目标产物。本发明还提供一种包括所述1‑甲基‑4‑(2‑甲基‑2H‑四氮唑‑5‑基)‑1H‑吡唑‑5‑磺酰胺的制备的四唑嘧磺隆的制备方法。本发明的制备方法反应路线短、反应原料环保、产率高。
• [EN] ARYL-BIPYRIDINE AMINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'AMINE ARYL-BIPYRIDINE UTILISÉS EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL PHOSPHATE KINASE
  申请人：PETRA PHARMA CORP

  公开号：WO2019126733A1

  公开（公告）日：2019-06-27

  The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I): wherein A, X, Y, Z, Q, R1, R2, R3, R4, R5, and n are described herein.

  这项发明涉及PI5P4K抑制剂，用于治疗癌症、神经退行性疾病、炎症性疾病和代谢性疾病，其化学式为（I）：其中A、X、Y、Z、Q、R1、R2、R3、R4、R5和n如本文所述。
• Synthesis and properties of sildenafil isostere
  作者：Ziqi Su、Qi Zhang、Qieqiang Zhao、Wenyi Liu、Tao Zhao、Huiping Wang、Jiarong Li、Juan Xu

  DOI：10.1002/ardp.202100145

  日期：2021.10

  series of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized and evaluated for their anti-phosphodiesterase-5 (PDE-5) activity. A total of 28 compounds, containing alkyl and aryl groups at the 1-N and 3-C positions on the pyrazole ring, and also bearing different alkyl substituents on the piperazine ring were synthesized. Four compounds (4d, 5d, 6d, and 5o) were found to have better

  合成了一系列新型吡唑并[3,4- d ]嘧啶-4-酮衍生物，并评估了它们的抗磷酸二酯酶5 (PDE-5) 活性。共合成了 28 种化合物，它们在吡唑环的 1-N 和 3-C 位含有烷基和芳基，在哌嗪环上也带有不同的烷基取代基。发现四种化合物（4d、5d、6d和5o）对 PDE-5 具有更好的抑制活性（IC 50  < 10 nM）。所有四种最活跃的化合物都在 N1 位包含一个苯环。含有 3,5-二甲基哌嗪基的化合物比其他化合物表现出更好的活性。这些结果表明化合物5o可用作开发新的 PDE-5 抑制剂的先导结构。
• [EN] PROCESS OF PREPARATION OF AZIMSULFURON<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AZIMSULFURON
  申请人：RALLIS INDIA LTD

  公开号：WO2014002111A1

  公开（公告）日：2014-01-03

  The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, (Formula I should be inserted here.) with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有化学式I的化合物（应在此处插入化学式I）与水杨酸或甲酸和氯气或次氯酸钠在氯化溶剂（如二氯甲烷、1,2-二氯乙烷）中，在氯化溶剂中的氯化氢的存在下处理，或者与水杨酸和N-氯琥珀酰亚胺或过氧化氢在环氧乙醚（如四氢呋喃、1,4-二噁烷）中的氯化氢的存在下处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。
• Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogs of 1-methylisoguanosine
  作者：Fiona A. Harden、Ronald J. Quinn、Peter J. Scammells

  DOI：10.1021/jm00113a031

  日期：1991.9

  Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents

  吡唑并[3,4-d]嘧啶是嘌呤的吡唑并类似物。它们已被证明是一类具有A1腺苷受体亲和力的化合物。已经合成了两个系列的1-甲基异鸟苷的吡唑并[3，4-d]嘧啶类似物。第一个涉及N1位置的取代，而第二个涉及N5位置的取代。检查了烷基和芳基取代基。通过使用（R）-[3H] -N6-（苯基异丙基）腺苷结合测定法测试所有化合物的A1腺苷受体亲和力。3-氯苯基在N1位上显示最大活性，而丁基在N5位上显示最大活性。在这些位置的每一个中最好的取代基的组合增强了整体活性。最有效的化合物是4-氨基-5-N-丁基-1-（3-氯苯基）-1H-吡唑并[3,4-d]嘧啶-6（5H）-，IC50为6.4 x 10（- 6）M.通过用[3H] CGS 21680进行A2腺苷受体亲和力测定，检查了在受体亚类上的选择性。这一系列化合物对A2受体的效力稍弱。4-氨基-5-N-丁基-1-（3-氯苯基-1H-吡唑并[3,4-d]嘧

表征谱图