4-溴噻唑-2-甲酸叔丁酯 | 944804-88-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-溴噻唑-2-甲酸叔丁酯
• 英文名称: tert-butyl (4-bromothiazol-2-yl)carbamate
• 英文别名: tert-butyl N-(4-bromo-1,3-thiazol-2-yl)carbamate；tert-Butyl 4-bromothiazol-2-ylcarbamate
• CAS: 944804-88-0
• 化学式: C₈H₁₁BrN₂O₂S
• 分子量: 279.158
• InChiKey: OVRIFGLINJVMLO-UHFFFAOYSA-N

物化性质

• 密度：
  1.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 4-bromothiazol-2-ylcarbamate
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: tert-Butyl 4-bromothiazol-2-ylcarbamate
CAS number: 944804-88-0

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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.
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: C8H11BrN2O2S
Molecular weight: 279.2

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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, 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：

  4-溴噻唑-2-甲酸叔丁酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 potassium acetate 、 palladium diacetate 、 caesium carbonate 、 三环己基膦 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 tert-butyl (4-methoxybenzyl)(4-(4-(trifluoromethyl)pyridin-2-yl)-thiazol-2-yl)carbamate
  参考文献：
  名称：

  3,4-取代的5-氨基吡唑和4-取代的-2-氨基噻唑的制备

  摘要：

  3,4-取代的5-氨基吡唑和4-取代的2-氨基噻唑是药物化学和药物开发项目中经常使用的中间体。我们报道了基于钯介导的β-酮腈与芳基溴化物的α-芳基化反应的3,4-取代的5-氨基吡唑类化合物的便捷合成（35个例子）。通过使用新制备的，适当保护的4-硼酸-2-氨基噻唑的频哪醇酯和MIDA酯与（杂）芳基卤化物的Suzuki偶联的序列，组装4-取代的2-氨基噻唑的文库（21个实例）。

  DOI：

  10.1021/acs.joc.8b02655
• 作为产物：
  描述：

  N-BOC-2-氨基-5-溴噻唑 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以91 %的产率得到4-溴噻唑-2-甲酸叔丁酯
  参考文献：
  名称：

  使用多功能 Boc 中间体方便合成 2-酰氨基-4-卤代噻唑和酰化衍生物

  摘要：

  2-氨基噻唑基团是许多系列生物活性分子的显着特征，包括抗生素、抗癌剂和非甾体抗炎药。我们对噻唑烷类化合物的合成和生物学评价有着长期的兴趣，即。 [2-羟基芳酰基-N- (噻唑-2-基)-酰胺]具有广谱抗感染，尤其是抗病毒特性。然而，2-氨基-4-取代的噻唑，尤其是4-卤代的噻唑，不容易获得。我们现在报道了从容易获得的拟硫代乙内酰脲或 2-氨基噻唑-4(5 H )-酮中实际、高效地合成此类物质：关键中间体是其 Boc 衍生物，在 Appel 相关条件下，从中可生成 Br、Cl 和 I都可以在C(4)处引入。虽然 2-氨基-4-Br/4-Cl 噻唑在酰化时产生的混合产物（包括双酰基产物）产率较低，但 Boc 中间体的进一步酰化，以及最后的温和脱保护步骤，干净且快速地提供了所需的噻唑烷类化合物。良好的产量。相反，即使2-乙酰氨基-4-氯噻唑轻微水解也会导致分解并快速回复为2-氨基噻唑-4(5 H

  DOI：

  10.1039/d4ra04959d

文献信息

• Modulators of Cystic Fibrosis Transmembrane Conductance Regulator
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20160095858A1

  公开（公告）日：2016-04-07

  The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

  本发明涉及一种具有以下化学式I的化合物： 或其药用可接受的盐，其中R 1 ，R 2 ，R 3 ，W，X，Y，Z，n，o，p和q在此处定义，用于治疗CFTR介导的疾病，如囊性纤维化。本发明还涉及药物组合物、治疗方法和相关工具包。
• ALKYLSULFONYL-SUBSTITUTED THIAZOLIDE COMPOUNDS
  申请人：Rossignol Jean-Francois

  公开号：US20090036467A1

  公开（公告）日：2009-02-05

  A new class of alkylsulfonyl-substituted thiazolide compounds is described. These compounds show strong activity against hepatitis virus.

  描述了一类新的烷基亚磺酰基取代的噻唑啉化合物。这些化合物对肝炎病毒表现出强烈的活性。
• Discovery of 4-(((4-(5-chloro-2-(((1s,4s)-4-((2-methoxyethyl)amino)cyclohexyl)amino)pyridin-4-yl)thiazol-2-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile (JSH-150) as a novel highly selective and potent CDK9 kinase inhibitor
  作者：Beilei Wang、Jiaxin Wu、Yun Wu、Cheng Chen、Fengming Zou、Aoli Wang、Hong Wu、Zhenquan Hu、Zongru Jiang、Qingwang Liu、Wei Wang、Yicong Zhang、Feiyang Liu、Ming Zhao、Jie Hu、Tao Huang、Juan Ge、Li Wang、Tao Ren、Yuxin Wang、Jing Liu、Qingsong Liu

  DOI：10.1016/j.ejmech.2018.09.025

  日期：2018.10

  Through a structure-guided rational drug design approach, we have discovered a highly selective inhibitor compound 40 (JSH-150), which exhibited an IC50 of 1 nM against CDK9 kinase in the biochemical assay and achieved around 300–10000-fold selectivity over other CDK kinase family members. In addition, it also displayed high selectivity over other 468 kinases/mutants (KINOMEscan S score(1) = 0.01)

  通过结构指导的合理药物设计方法，我们发现了一种高度选择性的抑制剂化合物40（JSH-150），在生化分析中对CDK9激酶的IC 50为1 nM，相对于CDK9激酶具有约300-10000倍的选择性。其他CDK激酶家族成员。此外，它还显示出对其他468种激酶/突变体的高选择性（KINOMEscan S得分（1）= 0.01）。化合物40显示出对黑素瘤，神经母细胞瘤，肝癌，结肠癌，肺癌以及白血病细胞系的有效抗增殖作用。它可以剂量依赖性地抑制RNA Pol II的磷酸化，抑制MCL-1和c-Myc的表达，阻滞细胞周期并诱导白血病细胞凋亡。在MV4-11细胞接种的异种移植小鼠模型中，10 mg / kg剂量的40剂量几乎可以完全抑制肿瘤的进展。高选择性和良好的体内PK / PD特性表明40是研究CDK9介导的生理学和病理学的良好药理工具，也是白血病和其他癌症的潜在候选药物。
• [EN] FLUOROISOQUINOLINE SUBSTITUTED THIAZOLE COMPOUNDS AND METHODS OF USE<br/>[FR] THIAZOLES SUBSTITUÉS PAR FLUOROISOQUINOLÉINE ET LEURS MÉTHODES D'APPLICATION
  申请人：AMGEN INC

  公开号：WO2010083246A1

  公开（公告）日：2010-07-22

  The invention relates to thiazole compounds of Formula (I) and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such thiazole compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

  该发明涉及式(I)的噻唑化合物及其组合物，用于治疗由蛋白激酶B（PKB）介导的疾病，其中变量具有此处提供的定义。该发明还涉及在治疗与异常细胞生长、癌症、炎症和代谢紊乱相关的疾病状态中使用这种噻唑化合物和其组合物的治疗用途。
• [EN] VACCINE ADJUVANT<br/>[FR] ADJUVANT DE VACCIN
  申请人：UNIV CALIFORNIA

  公开号：WO2020086625A1

  公开（公告）日：2020-04-30

  Compounds useful as an adjuvant, e.g., formulas (I)-(VI) and uses thereof, for example, with immunogenic moieties or other adjuvants, are provided.

  提供了作为辅助剂有用的化合物，例如，公式（I）-（VI）及其用途，例如与免疫原性部分或其他辅助剂一起使用。