吡唑并[1,5-a]吡啶-2,3-二甲酸二甲酯 | 5825-71-8

• 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 - 吡唑并吡啶类
• 中文名称: 吡唑并[1,5-a]吡啶-2,3-二甲酸二甲酯
• 中文别名: 吡唑并[1,5-A]吡啶-2,3-二羧酸二甲酯
• 英文名称: dimethyl pyrazolo[1,5-a]pyridine-2,3-dicarboxylate
• 英文别名: pyrazolo[1,5-a]pyridine-2,3-dicarboxylic acid dimethyl ester
• CAS: 5825-71-8
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: NZJIUQJPKXRRHB-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  174-178/0.23mm
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090
• 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 干燥 |

SDS

Name:	Dimethyl pyrazolo[1 5-a]pyridine-2 3-dicarboxylate Material Safety Data Sheet
Synonym:
CAS:	5825-71-8

Section 1 - Chemical Product MSDS Name:Dimethyl pyrazolo[1 5-a]pyridine-2 3-dicarboxylate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5825-71-8	Dimethyl pyrazolo[1,5-a]pyridine-2,3-d	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5825-71-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: Pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 174 - 178 deg C @0.3mbar
Freezing/Melting Point: 66 - 67 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H10N2O4
Molecular Weight: 234.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong bases, amines, strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5825-71-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Dimethyl pyrazolo[1,5-a]pyridine-2,3-dicarboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 5825-71-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5825-71-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5825-71-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  吡唑并[1,5-a]吡啶-2,3-二甲酸二甲酯 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.58h， 生成 methyl 2-[3-(4-methoxybenzyl)ureido]pyrazolo[1,5-a]pyridine-3-carboxylate
  参考文献：
  名称：

  新型N-3-取代的Pyrido [1'，2'：1,5] pyrazolo [3,4-d] pyrimidine-2,4（1H，3H）-dione衍生物的简便合成

  摘要：

  摘要 通过简单的四步合成法合成了以前未知的N-3-取代的吡啶并[1'，2'：1,5]吡唑并[3,4- d ]嘧啶衍生物。从1-氨基吡啶鎓盐开始，乙炔二羧酸二甲酯缩合，然后进行完全区域选择性皂化，生成吡唑并[1,5- a ]吡啶单酯作为关键中间体。直接进行Curtius重排，然后进行胺缩合，得到尿素库。最终的嘧啶环闭合导致杂环结构的实现。这种直接的策略提供了一种有效的方法，可以轻松地访问稀有的三环支架和高度有价值的衍生物库。 通过简单的四步合成法合成了以前未知的N-3-取代的吡啶并[1'，2'：1,5]吡唑并[3,4- d ]嘧啶衍生物。从1-氨基吡啶鎓盐开始，乙炔二羧酸二甲酯缩合，然后进行完全区域选择性皂化，生成吡唑并[1,5- a ]吡啶单酯作为关键中间体。直接进行Curtius重排，然后进行胺缩合，得到尿素库。最终的嘧啶环闭合导致杂环结构的实现。这种直接的策略提供了一种有效的方法，可以

  DOI：

  10.1055/s-0033-1338514
• 作为产物：
  描述：

  吡啶 在 二苯基膦酰羟胺 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 吡唑并[1,5-a]吡啶-2,3-二甲酸二甲酯
  参考文献：
  名称：

  [EN] SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS
  [FR] COMPOSÉS SPIRO-OXADIAZOLINE EN TANT QU'AGONISTES DES RÉCEPTEURS DE L'ACÉTYLCHOLINE Α-7 NICOTINIQUE

  摘要：

  本发明涉及新型螺环-噁二唑啉化合物，适用作a7-nAChR的激动剂或部分激动剂，以及这些化合物和组合物的制备方法、药物组合物，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物。具体而言，涉及向需要的患者（例如患有认知缺陷和/或希望增强认知功能的患者）施用螺环-噁二唑啉cx7-nAChR激动剂或部分激动剂的方法，以使其获益。

  公开号：

  WO2015066371A1

文献信息

• [EN] PYRAZOLYLPYRIDINE ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTIVIRAUX DE PYRAZOLYLPYRIDINE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011050284A1

  公开（公告）日：2011-04-28

  Provided are compounds of Formula (I) and/or Formula (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

  提供的是公式(I)和/或公式(II)的化合物以及它们的药用可接受的盐、它们的药物组合物、它们的制备方法，以及它们用于治疗由黄病毒科病毒家族成员如丙型肝炎病毒(HCV)介导的病毒感染。
• Study on selectivity in the reaction of 2-substituted pyridinium- N -imines with dimethyl acetylenedicarboxylate
  作者：Vyacheslav I. Supranovich、Aleksey Yu. Vorob’ev、Gennady I. Borodkin、Yury V. Gatilov、Vyacheslav G. Shubin

  DOI：10.1016/j.tetlet.2016.01.092

  日期：2016.3

  Reactions of 2-X-pyridinium-N-imines (X = F, Cl, Br, CN, OPh, NH2, N-morpholine) with dimethyl acetylenedicarboxylate (DMAD) have been studied. In the case of X = Cl, Br, CN, OPh both 7-substituted- and 7-H-pyrazolo[1,5-a]pyridines are formed. The 7-H/7-X ratio usually increases with the growing solvent polarity. The reaction of N-amino-2-iminopyridine with DMAD gives substituted pyrido[1,2-b][1,2

  研究了2-X-吡啶鎓-N-亚胺（X = F，Cl，Br，CN，OPh，NH 2和N-吗啉）与乙炔二羧酸二甲酯（DMAD）的反应。在X ＝ Cl，Br，CN，OPh的情况下，同时形成7-取代的和7- H-吡唑并[1，5- a ]吡啶。7-H / 7-X比率通常随着溶剂极性的增加而增加。N-氨基-2-亚氨基吡啶与DMAD的反应得到取代的吡啶并[1,2- b ] [1,2,4]三嗪。
• Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions
  作者：Abdelaziz Ejjoummany、Rabia Belaroussi、Ahmed El Hakmaoui、Mohamed Akssira、Gérald Guillaumet、Frédéric Buron、Sylvain Routier

  DOI：10.3390/molecules23112740

  日期：——

  2′:1,5]pyrazolo[4,3-d]pyrimidine derivatives is reported. The series was developed from 1-aminopyridinium iodide, which afforded the key intermediate bearing two thiomethyl and amide functions, each of them useful for palladium catalyzed cross coupling reactions by alkyl sulfur release and C-O activation, respectively. The two regioselective and successive cross-coupling reactions were first carried out

  报道了一些新型二(杂)芳基化-3H-吡啶并[1',2':1,5]吡唑并[4,3-d]嘧啶衍生物的设计。该系列是从 1-氨基吡啶鎓碘化物发展而来的，它提供了带有两个硫甲基和酰胺功能的关键中间体，它们中的每一个都可用于钯催化的烷基硫释放和 CO 活化的交叉偶联反应。两个区域选择性和连续的交叉偶联反应首先通过原位 CO 活化在 C-4 中进行，然后通过甲基硫释放在 C-2 中进行。工艺优化提供了导致产品产量高的条件。评估了方法的范围和局限性，并对最终化合物进行了表征。
• Synthesis of 1,4-Disubstituted Pyrido[1′,2′:1,5]pyrazolo[3,4-<i>d</i>]pyridazines by Means of S_NAr and Palladium-Catalysed Reactions
  作者：Rabia Belaroussi、Ahmed El Hakmaoui、Nathalie Percina、Agnes Chartier、Mathieu Marchivie、Stéphane Massip、Christian Jarry、Mohamed Akssira、Gérald Guillaumet、Sylvain Routier

  DOI：10.1002/ejoc.201500294

  日期：2015.6

  The first efficient synthesis of various 1,4-disubstituted pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines is reported. The reactivity toward chlorine release at the C-1 and C-4 positions was investigated. SNAr and palladium-catalysed cross-coupling reactions were carried out, and conditions were optimised for each procedure. 1,4-Bis(het)aryl derivatives were obtained under a Suzuki cross-coupling procedure

  报道了各种 1,4-二取代吡啶并[1',2':1,5]吡唑并[3,4-d]哒嗪的首次有效合成。研究了在 C-1 和 C-4 位置释放氯的反应性。进行了 SNAr 和钯催化的交叉偶联反应，并针对每个程序优化了条件。1,4-双(杂)芳基衍生物是在铃木交叉偶联程序下获得的，而SNAr取代主要在C-1而不是C-4处实现。单取代的 C-4 吗啉衍生物用作起始材料以提供不对称的 1,4-二胺或 1-（杂）芳基-4-吗啉产物。
• Synthesis of pyridine N-imine complexes of methylcobaloxime and reactions of bis(dimethylglyoximato)methyl(Pyridine N-imine)cobalt with acid anyhydrides and acetylenedicarboxylic acid dimethyl ester
  作者：Yasushi Tsurita、Taro Saito、Yukiyoshi Sasaki

  DOI：10.1016/s0022-328x(00)81386-8

  日期：1980.12

  Pyridine N-imine complexes of methylcobaloxime, CH3Co(Hdmg)2(R1— C5HnN+N−H) (n = 4; R1 = H, 2-CH3, 3-CH3, 4-CH3: n = 3; R1 = 2,6-CH3), have been synthesized by the reaction of CH3Co(Hdmg)2S(CH3)2 with a pyridine N-imine which is generated from a pyridine, hydroxylamine-O-sulfonic acid and K2CO3. The reactions of CH3Co(Hdmg)2(C5H5N+N−H) with acid anhydrides form new methylcobaloxime complexes with N-substituted

  吡啶Ñ methylcobaloxime的-亚胺配合物，CH 3的Co（Hdmg）2（R 1 - Visual C 5 ħ Ñ Ñ + N - H）（Ñ = 4; R 1 = H，2-CH 3，3-CH 3， 4-CH 3：n = 3； R 1 = 2,6-CH 3），是通过CH 3 Co（Hdmg）2 S（CH 3）2与吡啶N-亚胺的反应合成的吡啶，羟胺-O-磺酸和K 2 CO 3。CH 3 Co（Hdmg）2（C 5 H 5 N + N - H）与酸酐的反应与N-取代的吡啶N-亚胺形成新的甲基钴肟配合物，CH 3 Co（Hdmg）2（C 5 H 5 N + N - R 2）R 2 = COPh，COMe，COEt）。与马来酸酐，（吡啶N生成-丙烯酰亚胺基羧酸。用乙炔二羧酸二甲酯，配体的1，3-偶极环加成得到吡唑并[1，5-a]吡啶-2，3-二羧酸二甲酯。