ethyl 7-oxo-4H-pyrazolo[1,5-a]pyrimidine-6-carboxylate | 29274-18-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: ethyl 7-oxo-4H-pyrazolo[1,5-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate；7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester；7-Oxo-6-aethoxycarbonyl-4,7-dihydro-pyrazolo<1,5-a>pyrimidin
• CAS: 29274-18-8
• 化学式: C₉H₉N₃O₃
• mdl: MFCD00104600
• 分子量: 207.189
• InChiKey: KCRIHOOVSNHMLN-UHFFFAOYSA-N

物化性质

• 熔点：
  295-296 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  365.5±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  76.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-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: Ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate
CAS number: 29274-18-8

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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.
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: C9H9N3O3
Molecular weight: 207.2

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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.

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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：

  ethyl 7-oxo-4H-pyrazolo[1,5-a]pyrimidine-6-carboxylate 在 sodium hydroxide 、 diphenyl ether-biphenyl eutectic 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 4H-吡唑并[1,5-a]嘧啶-7-酮
  参考文献：
  名称：

  吡唑并[1,5-α]嘧啶酮区域异构体的合成

  摘要：

  这项工作描述了制备吡唑并[1,5-α]嘧啶-7-ones的两种不同途径和两种制备吡唑并[1,5-α] pyrimidin-5-ones的途径。在制备嘧啶-5-酮区域异构体中使用1,3-二甲基尿嘧啶作为亲电子试剂代表了对先前报道结果的修正。另外，鉴定了制备该异构体的新反应并阐明了反应机理。这项工作为实验者提供了互补的合成途径，这些途径提供了嘧啶7-1或嘧啶5-5区域异构体。

  DOI：

  10.1021/jo062120g
• 作为产物：
  描述：

  diethyl 2-((1H-pyrazol-5-ylamino)methylene)malonate 在 diphenyl ether-biphenyl eutectic 作用下， 反应 2.0h， 以58%的产率得到ethyl 7-oxo-4H-pyrazolo[1,5-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  [EN] MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR
  [FR] MODULATEURS DE RÉGULATEUR DE CONDUCTANCE TRANSMEMBRANAIRE DE FIBROSE CYSTIQUE

  摘要：

  本发明涉及ATP结合盒（'ABC'）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节器，以及相关的组合物和方法。本发明还涉及利用这些CFTR调节剂治疗疾病的方法。

  公开号：

  WO2009076593A1

文献信息

• Synthesis of Pyrazolo[1,5-α]pyrimidinone Regioisomers
  作者：Lori K. Gavrin、Arthur Lee、Brian A. Provencher、Walter W. Massefski、Stephen D. Huhn、Gregory M. Ciszewski、Derek C. Cole、John C. McKew

  DOI：10.1021/jo062120g

  日期：2007.2.1

  work describes two distinct routes to prepare pyrazolo[1,5-α]pyrimidin-7-ones and two distinct routes to prepare pyrazolo[1,5-α]pyrimidin-5-ones. Use of 1,3-dimethyluracil as the electrophile in the preparation of the pyrimidin-5-one regioisomer represents a correction of previously reported results. Also, a novel reaction to prepare this isomer was identified and the reaction mechanism elucidated. This

  这项工作描述了制备吡唑并[1,5-α]嘧啶-7-ones的两种不同途径和两种制备吡唑并[1,5-α] pyrimidin-5-ones的途径。在制备嘧啶-5-酮区域异构体中使用1,3-二甲基尿嘧啶作为亲电子试剂代表了对先前报道结果的修正。另外，鉴定了制备该异构体的新反应并阐明了反应机理。这项工作为实验者提供了互补的合成途径，这些途径提供了嘧啶7-1或嘧啶5-5区域异构体。
• Acid Derivatives of Pyrazolo[1,5-a]pyrimidine as Aldose Reductase Differential Inhibitors
  作者：Francesco Balestri、Luca Quattrini、Vito Coviello、Stefania Sartini、Federico Da Settimo、Mario Cappiello、Roberta Moschini、Antonella Del Corso、Umberto Mura、Concettina La Motta

  DOI：10.1016/j.chembiol.2018.07.008

  日期：2018.11

  Aldose reductase (AKR1B1), the key enzyme of the polyol pathway, plays a crucial role in the development of long-term complications affecting diabetic patients. Nevertheless, the expedience of inhibiting this enzyme to treat diabetic complications has failed, due to the emergence of side effects from compounds under development. Actually AKR1B1 is a Janus-faced enzyme which, besides ruling the polyol

  醛糖还原酶（AKR1B1）是多元醇途径的关键酶，在影响糖尿病患者的长期并发症的发生中起着至关重要的作用。然而，由于正在开发的化合物的副作用的出现，抑制这种酶治疗糖尿病并发症的方法失败了。实际上，AKR1B1是一种面对Janus的酶，除了决定多元醇途径外，还参与人体的抗氧化防御机制。在这项工作中，我们报告的证据表明，以吡唑并[1,5-a]嘧啶核和可电离片段为特征的一类化合物根据特定底物（例如糖）的存在而不同地调节酶的催化活性。 ，有毒醛和有毒醛的谷胱甘肽共轭物。
• Modulators of cystic fibrosis transmembrane conductance regulator
  申请人：Binch Hayley

  公开号：US08552006B2

  公开（公告）日：2013-10-08

  The present invention relates to compounds of formula IVA, formula IVB, or formula IVC, useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating diseases using such CFTR modulators.

  本发明涉及公式IVA、公式IVB或公式IVC化合物，这些化合物可作为ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节因子，以及这些化合物的组合物和使用这些组合物治疗疾病的方法。
• MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20140073653A1

  公开（公告）日：2014-03-13

  The present invention relates to compounds of formula IVA, formula IVB, or formula IVC, useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating diseases using such CFTR modulators.

  本发明涉及公式IVA、公式IVB或公式IVC的化合物，它们可作为ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节因子，以及这些化合物的组合物和使用它们的方法。本发明还涉及使用这些CFTR调节剂治疗疾病的方法。
• 4-Quinolone Derivatives:  High-Affinity Ligands at the Benzodiazepine Site of Brain GABA_A Receptors. Synthesis, Pharmacology, and Pharmacophore Modeling
  作者：Erik Lager、Pierre Andersson、Jakob Nilsson、Ingrid Pettersson、Elsebet Østergaard Nielsen、Mogens Nielsen、Olov Sterner、Tommy Liljefors

  DOI：10.1021/jm058057p

  日期：2006.4.1

  The 3-ethoxycarbonyl-4-quinolone compound I has previously been identified via a database search as an interesting lead compound for ligand binding at the benzodiazepine site of GABA(A) receptors (Kahnberg et al. J. Mol. Graphics Modelling 2004, 23, 253-261). Pharmacophore-guided optimization of this lead compound yielded a number of high-affinity ligands for the benzodiazepine site including compounds 20 and 23-25 displaying sub-nanomolar affinities. A few of the compounds have been tested on the alpha(1)beta(2)gamma(2s) and alpha(3)beta(2)gamma(2s) GABA(A) receptor subtypes, and two of the compounds (5 and 19) display selectivity for alpha(1) versus alpha(3)-containing receptors by a factor of 22 and 27, respectively. This selectivity for alpha(1)beta(2)gamma(2s) is in the same range as that for the well-known alpha(1) subunit selective compound zolpidem.