6-(叔丁基)-3-乙基-2-氨基-4,7-二氢噻吩[2,3-C]吡啶二甲酸叔丁酯 | 193537-14-3

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 中文名称: 6-(叔丁基)-3-乙基-2-氨基-4,7-二氢噻吩[2,3-C]吡啶二甲酸叔丁酯
• 中文别名: 2-氨基-4,7-二氢-5H-噻吩并[2,3-c]吡啶-3,6-二甲酸6-叔丁酯3-乙酯；2-氨基-4,7-二氢噻吩[2,3-C]吡啶-6-BOC-3-羧酸乙酯；2-氨基-4,7-二氢噻吩并[2,3-c]吡啶-3,6(5H)-二羧酸-6-(1,1-二甲基乙基)-3-乙酯；2-氨基-6-BOC-4,7-二氢噻吩并[2,3-C]吡啶-3(5H)-乙酸乙酯；2-氨基-4,7-二氢-5H-噻吩并[2,3-c]吡啶-3,6-二甲酸-6-叔丁酯-3-乙酸乙酯
• 英文名称: 6-(tert-butyl) 3-ethyl 2-amino-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxylate
• 英文别名: 6-tert-butyl 3-ethyl 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate；Ethyl 6-boc-2-amino-4,7-dihydro-5h-thieno[2,3-c]pyridine-3-carboxylate；6-O-tert-butyl 3-O-ethyl 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyridine-3,6-dicarboxylate
• CAS: 193537-14-3
• 化学式: C₁₅H₂₂N₂O₄S
• mdl: MFCD05664039
• 分子量: 326.417
• InChiKey: XSXVOVXVHBSSSN-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C
• 沸点：
  492.5±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 6-Boc-2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3-carboxylate
Synonyms: 2-Amino-4,7-dihydro-5h-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert butyl ester 3-ethyl es-
ter

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
Store locked up
P405:

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Section 3. Composition/information on ingredients.
Ingredient name: Ethyl 6-Boc-2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3-carboxylate
CAS number: 193537-14-3

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.

---

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.

---

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: C15H22N2O4S
Molecular weight: 326.4

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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, sulfur oxides.

---

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.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-(叔丁基)-3-乙基-2-氨基-4,7-二氢噻吩[2,3-C]吡啶二甲酸叔丁酯 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
  参考文献：
  名称：

  Thiophene inhibitors of PDE4: Crystal structures show a second binding mode at the catalytic domain of PDE4D2

  摘要：

  PDE4 inhibitors have been identified as therapeutic targets for a variety of conditions, particularly inflammatory diseases. We have serendipitously identified a novel class of phosphodiesterase 4 (PDE4) inhibitor during a study to discover antagonists of the parathyroid hormone receptor. X-ray crystallographic studies of PDE4D2 complexed to four potent inhibitors reveal the atomic details of how they inhibit the enzyme and a notable contrast to another recently reported thiophene-based inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.109
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 、 氰乙酸乙酯 在 sulfur 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 6-(叔丁基)-3-乙基-2-氨基-4,7-二氢噻吩[2,3-C]吡啶二甲酸叔丁酯
  参考文献：
  名称：

  PET探针检测易受表皮生长因子受体酪氨酸激酶抑制剂治疗的非小细胞肺癌

  摘要：

  表皮生长因子受体（EGFR-TKIs）的酪氨酸激酶抑制剂被用作非小细胞肺癌（NSCLC）患者的分子靶向治疗。该疗法适用于具有EGFR原发性L858R突变的患者，但由EGFR继发性突变引起的药物耐受性发生在一年半之内。为了通过正电子发射断层扫描（PET）成像无创检测EGFR-TKIs阳性患者，新合成了氟18标记的噻吩并嘧啶衍生物[ 18 F] FTP2。EGFR抑制试验，细胞摄取研究和阻断研究表明[ 18 F] FTP2对具有L858R突变的EGFR具有高选择性的亲和力，而不与L858R / T790M双突变结合。在使用荷瘤小鼠的动物PET研究中，表达L858R突变EGFR的H3255细胞比表达L858R / T790M双突变EGFR的H1975细胞更清晰可见。[ 18 F] FTP2具有检测对EGFR-TKI治疗敏感的NSCLC的潜力。

  DOI：

  10.1016/j.bmc.2018.02.007

文献信息

• Structure based design, synthesis and evaluation of new thienopyrimidine derivatives as anti-bacterial agents
  作者：Satyaveni Malasala、Anusha Polomoni、Md. Naiyaz Ahmad、Manjulika Shukla、Grace Kaul、Arunav Dasgupta、Sidharth Chopra、Srinivas Nanduri

  DOI：10.1016/j.molstruc.2021.130168

  日期：2021.6

  A number of TrmD inhibitors including thienopyrimidines and fused thienopyrimidines are reported as potent anti-bacterial and anti-mycobacterial agents. In the current study, a library of ~200 structurally diverse thienopyrimidines were designed and subjected to preliminary in silico studies. 22 of the compounds were selected, synthesized and were evaluated for their inhibitory activities against

  TrmD，tRNA-（N 1 G37）甲基转移酶是SPoU-TrmD（SPOUT）RNA甲基转移酶家族的成员，是负责金黄色葡萄球菌，铜绿假单胞菌，结核分枝杆菌（Mtb）和脓肿分枝杆菌（单抗）。据报道，许多TrmD抑制剂包括噻吩并嘧啶和稠合的噻吩并嘧啶，它们是有效的抗菌剂和抗分枝杆菌剂。在当前的研究中，设计了一个约200个结构多样化的噻吩并嘧啶的文库，并进行了初步的计算机模拟研究。选择，合成了22种化合物，并评估了其对一组病原体的抑制活性大肠杆菌，金黄色葡萄球菌，肺炎克雷伯氏菌，鲍曼不动杆菌和铜绿假单胞菌和结核分枝杆菌（ATCC 27294）。在被测化合物中，发现MIC为16-32 µg / mL的13b，18a-e可抑制结核分枝杆菌（ATCC 27294）。发现化合物18f对金黄色葡萄球菌具有选择性，MIC为4μg/ mL，对结核分枝杆菌具有中等活性。对选定的化合物进一步进行对接，3D-QSAR和ADME
• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• [EN] SUBSTITUTED TRICYCLIC COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS TRICYCLIQUES SUBSTITUÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：BAYER HEALTHCARE AG

  公开号：WO2009033581A1

  公开（公告）日：2009-03-19

  This invention relates to novel compounds and processes for their preparation, methods of treating diseases, particularly cancer, comprising administering said compounds, and methods of making pharmaceutical compositions for the treatment or prevention of disorders, particularly cancer.

  这项发明涉及新颖化合物及其制备方法，治疗疾病的方法，特别是癌症，包括给予这些化合物，以及制备用于治疗或预防疾病，特别是癌症的药物组合物的方法。
• Fused Bicyclic and Tricyclic Pyrimidine Compounds as Tyrosine Kinase Inhibitors
  申请人：Hsieh Hsing-Pang

  公开号：US20100120805A1

  公开（公告）日：2010-05-13

  Fused bicyclic or tricyclic compounds of formula (I): wherein A, B, C, X, Y, m, and n are defined herein. Also disclosed are a method for inhibiting EGFR kinase activity and a method for treating cancer with these compounds.

  式(I)的融合双环或三环化合物： 其中A、B、C、X、Y、m和n在此处定义。还公开了一种抑制EGFR激酶活性的方法以及使用这些化合物治疗癌症的方法。
• [EN] FUSED THIOPHENE DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS DE THIOPHÈNE CONDENSÉS ET LEURS UTILISATIONS
  申请人：ENYO PHARMA

  公开号：WO2019154949A1

  公开（公告）日：2019-08-15

  The present invention relates to a new class of fused thiophene derivatives and their uses for treating diseases such as infection, cancer, metabolic diseases, cardiovascular diseases, iron storage disorders and inflammatory disorders.

  本发明涉及一类新的融合噻吩衍生物，以及它们在治疗感染、癌症、代谢性疾病、心血管疾病、铁储存障碍和炎症性疾病方面的用途。