3,5-二甲基-1-氢-吡咯-2-羧酸叔丁酯-4-羧酸乙酯 | 86770-31-2

• 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 - 吡咯
• 中文名称: 3,5-二甲基-1-氢-吡咯-2-羧酸叔丁酯-4-羧酸乙酯
• 中文别名: 1H-吡咯-2,4-二甲酸；3,5-二甲基-1H-吡咯-2-羧酸叔丁酯-4-羧酸乙酯；3,5-二甲基吡咯-2-羧酸叔丁酯-4-羧酸乙酯；舒尼替尼中间体1；1H-吡咯-2,4-二甲酸,3,5-二甲基-,2-(1,1-二甲基乙基)4-乙酯；舒尼替尼中间体 1
• 英文名称: 2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
• 英文别名: 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester；2-O-tert-butyl 4-O-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
• CAS: 86770-31-2
• 化学式: C₁₄H₂₁NO₄
• mdl: MFCD02179394
• 分子量: 267.325
• InChiKey: CJXJFSNESZDOGK-UHFFFAOYSA-N

物化性质

• 沸点：
  386.8±37.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,5-Dimethyl-1h-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester
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: 3,5-Dimethyl-1h-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester
CAS number: 86770-31-2

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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: C14H21NO4
Molecular weight: 267.3

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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：

  3,5-二甲基-1-氢-吡咯-2-羧酸叔丁酯-4-羧酸乙酯 在 四氢吡咯 盐酸 、 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 为溶剂， 反应 32.5h， 生成 舒尼替尼
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF HIGH PURITY SUNITINIB AND ITS PHARMACEUTICALLY ACCEPTABLE SALT

  摘要：

  本发明涉及一种改进的制备N-[2-(二乙基氨基)乙基]-5-[(Z)-(5-氟-1,2-二氢-2-氧-3H-吲哚-3-基亚甲基)-2,4-二甲基-1H-吡咯-3-羧酰胺—Sunitinib（化学式(I)）及其药用可接受的苹果酸盐（化学式(I(a)）的过程。

  公开号：

  US20110092717A1
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 锌 作用下， 以 水 为溶剂， 反应 5.0h， 以24.7%的产率得到3,5-二甲基-1-氢-吡咯-2-羧酸叔丁酯-4-羧酸乙酯
  参考文献：
  名称：

  WO2008/33743

  摘要：

  公开号：

文献信息

• Formulations for pharmaceutical agents ionizable as free acids or free bases
  申请人：Shenoy Narmada

  公开号：US06878733B1

  公开（公告）日：2005-04-12

  The present invention features formulations of indolinones which compounds are ionizable as free acids or free bases. The formulation is suitable for parenteral or oral administration, wherein the formulation comprises an ionizable substituted indolinone, and a pharmaceutically acceptable carrier therefor. The term “ionizable substituted indolinone” includes pyrrole substituted 2-indolinones which, in addition to being otherwise optionally substituted on both the pyrrole and 2-indolinone portions of the compound, are necessarily substituted on the pyrrole moiety with one or more hydrocarbon chains which themselves are substituted with at least one polar group. The formulations and the compounds themselves are useful for the treatment of protein kinase related disorders as discussed herein.

  本发明涉及吲哚酮的配方，这些化合物作为游离酸或游离碱是可离子化的。该配方适用于静脉或口服给药，其中配方包括可离子化的取代吲哚酮和其药用可接受载体。术语“可离子化的取代吲哚酮”包括吡咯取代的2-吲哚酮，除了在化合物的吡咯和2-吲哚酮部分上可选择地被取代外，必须在吡咯基上用一个或多个烃链取代，这些烃链本身被至少一个极性基团取代。如本文所述，这些配方和化合物本身对于治疗蛋白激酶相关疾病是有用的。
• PYRROLO-NITROGENOUS HETEROCYCLIC DERIVATIES,THE PREPARATION AND THE PHARMCETICAL USE THEEOF
  申请人：ChoTang Peng Cho

  公开号：US20100075952A1

  公开（公告）日：2010-03-25

  The invention provides new pyrrolo-nitrogenous heterocyclic derivatives represented by formula (I) or their salts, the preparation thereof, pharmaceutical compositions containing such derivatives and the use of such derivatives as therapeutic agents, especially as protein kinase inhibitors, wherein each substituent in formula (I) is same as defined in the description.

  该发明提供了由式(I)表示的新的吡咯基氮杂环衍生物或其盐，其制备方法，含有这种衍生物的药物组合物以及将这种衍生物用作治疗剂，特别是蛋白激酶抑制剂的用途，其中式(I)中的每个取代基与描述中定义的相同。
• Design, synthesis and biological activities of pyrrole-3-carboxamide derivatives as EZH2 (enhancer of zeste homologue 2) inhibitors and anticancer agents
  作者：Qifan Zhou、Lina Jia、Fangyu Du、Xiaoyu Dong、Wanyu Sun、Lihui Wang、Guoliang Chen

  DOI：10.1039/c9nj04713a

  日期：——

  Zeste enhancer homolog 2 (EZH2) is highly expressed in various malignant tumors, which could silence tumor suppressor genes via trimethylation of H3K27. Herein was first reported a novel series of pyrrole-3-carboxamide derivatives carrying a pyridone fragment as EZH2 inhibitors. By combining computational modeling, in vitro cellular assays and further rational structure–activity relationship exploration

  Zeste增强子同源物2（EZH2）在各种恶性肿瘤中高表达，可以通过H3K27的三甲基化沉默沉默抑癌基因。本文首先报道了一系列带有吡啶酮片段作为EZH2抑制剂的吡咯-3-羧酰胺衍生物。通过将计算模型，体外细胞分析以及进一步的合理的构效关系探索和优化相结合，化合物DM-01对EZH2具有强大的抑制作用。在蛋白质印迹试验中，发现DM-01具有降低K562细胞中细胞H3K27me3水平的显着能力。同时，我们的数据显示，敲低A549细胞中的EZH2导致细胞对DM-01的敏感性降低在50和100μM下 DM-01还可以以剂量依赖的方式增加DIRAS3的转录表达，这是EZH2下游的一种抑癌剂，表明它有必要进一步研究作为先导化合物。
• Treatment of acute myeloid leukemia with indolinone compounds
  申请人：SUGEN, Inc.

  公开号：US20030130280A1

  公开（公告）日：2003-07-10

  A method of treating acute myeloid leukemia in patient positive for FLT-3-ITD is described. The treatment is accomplished by administration of a compound of Formula I or II as defined herein.

  描述了一种治疗FLT-3-ITD阳性患者急性髓系白血病的方法。该治疗通过给予本文中定义的I或II式化合物来实现。
• Treatment of excessive osteolysis with indolinone compounds
  申请人：SUGEN, INC.

  公开号：US20040209937A1

  公开（公告）日：2004-10-21

  Compounds of Formula I and Formula II, as described herein, are useful for treating excessive osteolysis, by inhibiting M-CSF mediated osteoclast development. The compounds also are useful for inhibiting phosphorylation of CSF1R, and for treating cancers that express CSF1R.

  本文描述的式I和式II的化合物可用于治疗过度骨溶解，通过抑制M-CSF介导的破骨细胞发育。这些化合物还可用于抑制CSF1R的磷酸化，并用于治疗表达CSF1R的癌症。