3-氨基-4-溴-噻吩-2-羧酸甲酯 | 161833-42-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-氨基-4-溴-噻吩-2-羧酸甲酯
• 中文别名: 3-氨基-4-溴噻吩-2-羧酸甲酯
• 英文名称: methyl 3-amino-4-bromothiophene-2-carboxylate
• CAS: 161833-42-7
• 化学式: C₆H₆BrNO₂S
• 分子量: 236.089
• InChiKey: LWSWLXPUUCBUPI-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±37.0 °C(Predicted)
• 密度：
  1.745±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  储存条件：2-8℃，干燥、密封并避光保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-amino-4-bromothiophene-2-carboxylate
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: Methyl 3-amino-4-bromothiophene-2-carboxylate
CAS number: 161833-42-7

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H6BrNO2S
Molecular weight: 236.1

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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, hydrogen bromide, sulfur 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：

  3-氨基-4-溴-噻吩-2-羧酸甲酯 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以97%的产率得到3-氨基-4-溴噻吩-2-羧酸
  参考文献：
  名称：

  三取代噻吩并[3,2-d]嘧啶衍生物的固相和固相合成新方法

  摘要：

  7-芳基-3,4-二氢-4-氧噻吩并[3,2- d ]嘧啶-2-羧酸与烷基胺负载的酸敏感的甲氧基苯甲醛（AMEBA）树脂（苯并三唑-1-酯）的偶联六氟磷酸基氧基三（二甲氨基）phosph （BOP）介导的胺化反应，并从固相支持物上裂解，得到N-烷基-4-（烷基氨基）-7-芳基硫代[3,2 - d ]嘧啶-2-羧酰胺衍生物。通过衰减全反射-FTIR光谱监测固相反应的进程，并将其与代表性的溶液相替代物进行比较。此外，N-酰化（酰氯，InF 3，CH 3CN，室温）和3-氨基-4-（4-叔丁氧基羰基苯基）噻吩-2-羧酰胺中间体在以前未报告的条件下的环化（DBN，1,4-二恶烷，80°C）提供了2-取代的硫代诺[3,2 - d ]嘧啶-4（3 H）-one衍生物，随后将其转化为2-取代的4-烷基氨基-7- [4-（烷基氨基羰基）苯基]噻吩并[3,2- d ]嘧啶衍生物通过由BOP介导的胺化反应，叔丁基脱保护和酰胺形成组成的反应顺序。

  DOI：

  10.1002/bkcs.10878
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 溴 、 溶剂黄146 作用下， 反应 20.0h， 以37%的产率得到3-氨基-4-溴-噻吩-2-羧酸甲酯
  参考文献：
  名称：

  三取代噻吩并[3,2-d]嘧啶衍生物的固相和固相合成新方法

  摘要：

  7-芳基-3,4-二氢-4-氧噻吩并[3,2- d ]嘧啶-2-羧酸与烷基胺负载的酸敏感的甲氧基苯甲醛（AMEBA）树脂（苯并三唑-1-酯）的偶联六氟磷酸基氧基三（二甲氨基）phosph （BOP）介导的胺化反应，并从固相支持物上裂解，得到N-烷基-4-（烷基氨基）-7-芳基硫代[3,2 - d ]嘧啶-2-羧酰胺衍生物。通过衰减全反射-FTIR光谱监测固相反应的进程，并将其与代表性的溶液相替代物进行比较。此外，N-酰化（酰氯，InF 3，CH 3CN，室温）和3-氨基-4-（4-叔丁氧基羰基苯基）噻吩-2-羧酰胺中间体在以前未报告的条件下的环化（DBN，1,4-二恶烷，80°C）提供了2-取代的硫代诺[3,2 - d ]嘧啶-4（3 H）-one衍生物，随后将其转化为2-取代的4-烷基氨基-7- [4-（烷基氨基羰基）苯基]噻吩并[3,2- d ]嘧啶衍生物通过由BOP介导的胺化反应，叔丁基脱保护和酰胺形成组成的反应顺序。

  DOI：

  10.1002/bkcs.10878

文献信息

• ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS
  申请人：Gokaraju Ganga Raju

  公开号：US20100068178A1

  公开（公告）日：2010-03-18

  The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.

  本发明公开了一般式(I)和式(II)的三氮烯类似物，其互变异构体、立体异构体、多晶形态、水合物、溶剂合物及其在转移性恶性黑色素瘤和其他癌症，包括但不限于淋巴瘤、肉瘤、癌瘤和胶质瘤中的药用可接受盐。该发明还公开了制备上述式(I)和式(II)的三氮烯类似物以及其药用可接受组合物的方法。
• FUSED PYRIMIDINE COMPOUND, INTERMEDIATE, PREPARATION METHOD THEREFOR, AND COMPOSITION AND APPLICATION THEREOF
  申请人：SHANGHAI YINGLI PHARMACEUTICAL CO., LTD

  公开号：US20160214994A1

  公开（公告）日：2016-07-28

  Disclosed are a fused pyrimidine compound, an intermediate, a preparation method therefor, and a composition and an application thereof. The present invention provides a fused pyrimidine compound shown in formula I, pharmaceutically acceptable salt, hydrate, solvate, and an optical isomer or prodrug of the compound. The present invention further provides applications of the fused pyrimidine compound shown in formula I, the pharmaceutically acceptable salt, the hydrate, solvate, and the optical isomer or the prodrug of the compound in the preparing drugs for curing and/or preventing a kinase-related disease. The fused pyrimidine compound I of the present invention is an efficient PI3 kinase depressor, and can be used to prepare drugs for preventing and/or curing cell-proliferation diseases such as cancer, infection, inflammation, and an autoimmune disease.

  揭示了一种融合嘧啶化合物，其中间体，制备方法以及其组成和应用。本发明提供了一种如式I所示的融合嘧啶化合物，该化合物的药用可接受盐，水合物，溶剂合物，以及光学异构体或前药。本发明还提供了应用式I所示的融合嘧啶化合物，药用可接受盐，水合物，溶剂合物，以及该化合物的光学异构体或前药在制备用于治疗和/或预防激酶相关疾病的药物中。本发明的融合嘧啶化合物I是一种高效的PI3激酶抑制剂，可用于制备用于预防和/或治疗细胞增殖性疾病，如癌症，感染，炎症和自身免疫疾病的药物。
• [EN] ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS D'ECTONUCLÉOTIDES PYROPHOSPHATASES/PHOSPHODIESTÉRASES 1 (ENPP1) ET LEURS UTILISATIONS
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2021133915A1

  公开（公告）日：2021-07-01

  Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

  本文提供了外胞核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）的小分子调节剂，包括这些化合物的组合物，以及使用这些化合物和包含这些化合物的组合物的方法。
• Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB₂ R Ligands
  作者：Hai-Yan Qian、Zhi-Long Wang、Li-Li Chen、You-Lu Pan、Xiao-Yu Xie、Xin Xie、Jian-Zhong Chen

  DOI：10.1002/cmdc.201800541

  日期：2018.11.20

  bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328‐fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality

  在本文中，我们基于喹诺林-2,4（1 H，3 H）-二酮作为CB 2 R-选择性配体，使用生物等排策略，描述了一系列新的杂芳基嘧啶/杂芳基三嗪衍生物的设计和合成。为了消除立体异构和增加亲水性，研究了乙酰胺基团取代了前导化合物的烯胺连接基。结果，一些合成的化合物在钙动员测定中显示出对CB 2 R的高生物活性和选择性，并且有四个显示出CB 2 R激动剂活性，EC 50值低于30 n m。该化合物对CB 2表现出最高的激动剂活性R（EC 50 = 7.53±3.15 n m）对CB 1 R的选择性超过1328倍。此外，结构-活性关系（SAR）研究表明，核上的取代基在配体的功能中起关键作用，其中一个例子证明了CB 2 R拮抗剂的活性。此外，进行分子对接模拟的目的是为了更好地了解这些新衍生物与结合CB 2 R的激动剂/拮抗剂的结构要求。
• [EN] COMPOUNDS THAT INTERACT WITH THE RAS SUPERFAMILY FOR THE TREATMENT OF CANCERS, INFLAMMATORY DISEASES, RASOPATHIES, AND FIBROTIC DISEASE<br/>[FR] COMPOSÉS INTERAGISSANT AVEC LA SUPERFAMILLE RAS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE CANCERS, DE MALADIES INFLAMMATOIRES, DE RASOPATHIES ET DE MALADIES FIBROTIQUES
  申请人：SHY THERAPEUTICS LLC

  公开号：WO2018237084A1

  公开（公告）日：2018-12-27

  Provided herein are methods and compositions for treating cancers, inflammatory diseases, rasopathies, and fibrotic disease involving aberrant Ras superfamily signaling through the binding of compounds to the GTP binding domain of Ras superfamily proteins including, in certain cases, K-Ras and mutants thereof, and a novel method for assaying such compositions.

  本发明提供了治疗癌症、炎症性疾病、rasopathy症和涉及异常Ras超家族信号传导的纤维化疾病的方法和组合物，这些方法和组合物通过化合物与Ras超家族蛋白（包括在某些情况下K-Ras及其突变体）的GTP结合域的结合来实现。此外，还提供了一种用于检测这些组合物的新方法。