4-氯-1,3-二甲基-1H-吡唑3,4-吡啶-5-羧酸 | 175201-94-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 4-氯-1,3-二甲基-1H-吡唑3,4-吡啶-5-羧酸
• 中文别名: 1,3-二甲基-4-氯-1H-吡唑[3,4-b]并吡啶-5-甲酸；4-氯-1,3-二甲基吡唑[3,4-b]吡啶-5-羧酸；4-氯-1,3-二甲基-1H-吡咯[3,4,B]吡啶-5-羧酸；1,3-二甲基-4-氯-1H-吡唑[3,4-B]并吡啶-5-甲酸；4-氯-1,3-二甲基-吡唑并[3,4-b]吡啶-5-甲酸
• 英文名称: 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
• 英文别名: 4-chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carboxylic acid；4-chloro-1,3-dimethylpyrazolo [5,4-b]pyridine-5-carboxylic acid；4-chloro-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carboxylic acid
• CAS: 175201-94-2
• 化学式: C₉H₈ClN₃O₂
• mdl: MFCD00067959
• 分子量: 225.634
• InChiKey: LHEUUYZQYKWDSY-UHFFFAOYSA-N

物化性质

• 熔点：
  269 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

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

SDS

Name:	4-Chloro-1 3-dimethyl-1H-pyrazolo[3 4-b]pyridine-5-carboxylic acid Material Safety Data Sheet
Synonym:
CAS:	175201-94-2

Section 1 - Chemical Product MSDS Name:4-Chloro-1 3-dimethyl-1H-pyrazolo[3 4-b]pyridine-5-carboxylic acid Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175201-94-2	4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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. Wash mouth out with 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:
Treat symptomatically and supportively.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
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# 175201-94-2: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 280 deg C (decom)
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: C9H8ClN3O2
Molecular Weight: 226

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, reducing agents, bases, acid chlorides, amines.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175201-94-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 175201-94-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175201-94-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175201-94-2 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：

  4-氯-1,3-二甲基-1H-吡唑3,4-吡啶-5-羧酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 4-氯-1,3-二甲基吡唑并[3,4-B]吡啶-5-羰酰氯
  参考文献：
  名称：

  杂环构件的简便方法：合成包含[5,6] Pyrano [2,3-c]吡唑-4（1H）-one的新型环系统。

  摘要：

  从可商购的离析物开始，通向三环，四环或五环体系的一步或两步合成是向新杂环构件的直接合成路线。以下新型环系统的代表是由3-甲基-1-苯基-2-吡唑啉-5-酮和相应的邻卤代芳烃羰基氯在回流的1,4-二恶烷中使用氢氧化钙制备的：嘧啶[4'， 5'：5,6] pyrano [2,3-c] pyrazol-4（1H）-one，thieno [3'，2'：5,6] pyrano [2,3c] pyrazol- 4-（1H）-一，thieno [3'，4'：5,6] pyrano [2,3-c] pyrazol-4（1H）-one，thieno [3''，2''：4'，5'] thieno [2 '，3'：5,6]-吡喃并[2,3-c]吡唑-4（1H）-one，[1,3] dioxolo [5'，6'] [1] benzothieno [2'，3' ：5,6] pyrano- [2,3-c]-pyraz

  DOI：

  10.3390/12010060
• 作为产物：
  描述：

  5-氨基-1,3-二甲基吡唑 在 氢氧化钾 、 三氯氧磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 37.0h， 生成 4-氯-1,3-二甲基-1H-吡唑3,4-吡啶-5-羧酸
  参考文献：
  名称：

  Discovery of New Orally Active Phosphodiesterase (PDE4) Inhibitors

  摘要：

  合成了一系列4-氨基吡唑并吡啶衍生物，并对其作为磷酸二酯酶（PDE4）抑制剂进行生物评估。对3这一我们内部库中发现的结构新颖的化学先导物的化学改造主要集中在1-和3-取代基上。本文详细介绍了新型口服活性化学先导物5的发现，以及结构-活性关系数据、药理评估和亚型选择性研究的结果。

  DOI：

  10.1248/cpb.52.1098

文献信息

• Hepatitis C virus inhibitors
  申请人：Hewawasam Piyasena

  公开号：US20070010455A1

  公开（公告）日：2007-01-11

  The present disclosure relates to tripeptide compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及三肽化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• Synthesis of γ-Oxo-α-amino Acids via Radical Acylation with Carboxylic Acids
  作者：Kay Merkens、Francisco José Aguilar Troyano、Khadijah Anwar、Adrián Gómez-Suárez

  DOI：10.1021/acs.joc.0c02951

  日期：2021.6.18

  light-mediated, deoxygenative protocol to access γ-oxo-α-amino acid derivatives. This radical methodology employs photoredox catalysis, in combination with triphenylphosphine, to generate acyl radicals from readily available (hetero)aromatic and vinylic carboxylic acids. This approach allows for the straightforward synthesis of γ-oxo-α-amino acids bearing a wide range of functional groups (e.g., Cl, CN,

  在此，我们提出了一种高效、光介导的脱氧方案来获取 γ-氧代-α-氨基酸衍生物。这种自由基方法采用光氧化还原催化，结合三苯基膦，从容易获得的（杂）芳香族和乙烯基羧酸生成酰基自由基。这种方法允许以合成有用的产率（~60% 平均产率）直接合成带有多种官能团（例如，Cl、CN、呋喃、噻吩、Bpin）的 γ-氧代-α-氨基酸。为了进一步突出该方法的实用性，进行了几个脱保护和衍生化反应。
• Discovery of New Orally Active Phosphodiesterase (PDE4) Inhibitors
  作者：Hiroshi Ochiai、Akiharu Ishida、Tazumi Ohtani、Kensuke Kusumi、Katuya Kishikawa、Susumu Yamamoto、Hiroshi Takeda、Takaaki Obata、Hisao Nakai、Masaaki Toda

  DOI：10.1248/cpb.52.1098

  日期：——

  A series of 4-anilinopyrazolopyridine derivatives were synthesized and biologically evaluated as inhibitors of phosphodiesterase (PDE4). Chemical modification of 3, a structurally new chemical lead that was found in our in-house library, was focused on 1- and 3-substituents. Full details of the discovery of a new orally active chemical lead 5 are presented. Structure–activity relationship data, pharmacological evaluation, and the subtype selectivity study are also presented.

  合成了一系列4-氨基吡唑并吡啶衍生物，并对其作为磷酸二酯酶（PDE4）抑制剂进行生物评估。对3这一我们内部库中发现的结构新颖的化学先导物的化学改造主要集中在1-和3-取代基上。本文详细介绍了新型口服活性化学先导物5的发现，以及结构-活性关系数据、药理评估和亚型选择性研究的结果。
• Preparation and use of ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors
  申请人：——

  公开号：US20010046989A1

  公开（公告）日：2001-11-29

  This invention provides, low molecular weight, non-peptide inhibitors of matrix metalloproteinases and TNF-&agr; converting enzyme (TACE, tumor necrosis factor-&agr; converting enzyme) of formula: B wherein B is 1 2 T, U, W, and X are each, independently, carbon or nitrogen, provided that when T or U is carbon, either may be optionally substituted with R 1 ; Y is carbon, nitrogen, oxygen or sulfur, provided that at least one of T, U, W, X, and Y is not carbon, and further provided that no more than 2 of T, U, W, and X are nitrogen; 3 is a phenyl ring or is a heteroaryl ring of ring 5-6 atoms which may contain 0-2 heteratoms selected from nitrogen, oxygen, and sulfur, in addition to any heteroatoms defined by W or X; wherein the phenyl or heteroaryl ring may be optionally mono-, di-, or tri- substituted with R 1 ; Z is a phenyl, naphthyl, heteroaryl, or heteroaryl fused to phenyl, wherein the heteroaryl moiety contains of 5-6 ring atoms and 1-3 heteroatoms selected from nitrogen, oxygen, or sulfur; wherein the phenyl, naphthyl, heteroaryl, or phenyl fused heteroaryl moieties may be optionally mono-, di-, or tri- substituted with R 1 ; R 1 is hydrogen, halogen, alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cyclocalkyl of 3-6 carbon atoms, —(CH 2 ) n Z, —OR 2 , —CN, —COR 2 , perfluoroalkyl of 1-4 carbon atoms, —CONR 2 R 3 , —S(O) x R 2 —OPO(OR 2 )OR 3 , —PO(OR 2 )R 3 , —OC(O)NR 2 R 3 , —COOR 2 , —CONR 2 R 3 , —SO 3 H, —NR 2 R 3 , —NR 2 COR 3 , —NR 2 COOR 3 , —SO 2 NR 2 R 3 , —NO 2 , —N(R 2 )SO 2 R 3 , —NR 2 CONR 2 R 3 , —NR 2 C(═NR 3 )NR 2 R 3 , —SO 2 NHCOR 4 , —CONHSO 2 R 4 , -tetrazol-5-yl, —SO 2 NHCN, —SO 2 NHCONR 2 R 3 or Z; V is a saturated or partially unsaturated heterocycloalkyl ring of 5-7 ring atoms having 1-3 heteroatoms selected from N, O, or S, which may be optionally mono-, or di-substituted with R 2 ; R 2 and R 3 are each, independently, hydrogen, alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 3-6 carbon atoms; perfluoroalkyl of 1-4 carbon atoms, Z or V; R 4 is alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 3-6 carbon atoms; perfluoroalkyl of 1-4 carbon atoms, Z or V; R 5 is hydrogen, alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, Z, or V; n=1-6; x=0-2 or a pharmaceutically acceptable salt thereof.

  这项发明提供了低分子量、非肽类的基质金属蛋白酶和TNF-α转化酶（TACE，肿瘤坏死因子-α转化酶）的抑制剂，其化学式为：其中 B 是 12T，U，W 和 X 分别独立地为碳或氮，但当 T 或 U 为碳时，可以选择性地用 R1 取代；Y 为碳、氮、氧或硫，要求 T、U、W、X 和 Y 中至少有一个不是碳，并且进一步要求 T、U、W 和 X 中不超过 2 个是氮；3 为苯环或是由 5-6 个原子组成的杂环，其中可能含有 0-2 个氮、氧或硫等杂原子，除了 W 或 X 定义的杂原子之外；苯或杂环可能选择性地单取代、双取代或三取代的 R1；Z 为苯、萘、杂环或与苯融合的杂环，其中杂环部分含有 5-6 个环原子和 1-3 个氮、氧或硫等杂原子；苯、萘、杂环或苯融合杂环部分可能选择性地单取代、双取代或三取代的 R1；R1 为氢、卤素、1-8 个碳原子的烷基、2-6 个碳原子的烯基、2-6 个碳原子的炔基、3-6 个碳原子的环烷基、—(CH2)nZ、—OR2、—CN、—COR2、1-4 个碳原子的全氟烷基、—CONR2R3、—S(O)xR2—OPO(OR2)OR3、—PO(OR2)R3、—OC(O)NR2R3、—COOR2、—CONR2R3、—SO3H、—NR2R3、—NR2COR3、—NR2COOR3、—SO2NR2R3、—NO2、—N(R2)SO2R3、—NR2CONR2R3、—NR2C(═NR3)NR2R3、—SO2NHCOR4、—CONHSO2R4、-四唑-5-基、—SO2NHCN、—SO2NHCONR2R3 或 Z；V 为由 5-7 个环原子组成、含有 1-3 个氮、氧或硫等杂原子的饱和或部分不饱和杂环烷基，可能选择性地单取代或双取代的 R2；R2 和 R3 分别独立地为氢、1-8 个碳原子的烷基、2-6 个碳原子的烯基、2-6 个碳原子的炔基、3-6 个碳原子的环烷基、1-4 个碳原子的全氟烷基、Z 或 V；R4 为1-8 个碳原子的烷基、2-6 个碳原子的烯基、2-6 个碳原子的炔基、3-6 个碳原子的环烷基、1-4 个碳原子的全氟烷基、Z 或 V；R5 为氢、1-8 个碳原子的烷基、2-6 个碳原子的烯基、2-6 个碳原子的炔基、Z 或 V；n=1-6；x=0-2 或其药用盐。
• Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors
  申请人：American Cyanamid Company

  公开号：US20030208066A1

  公开（公告）日：2003-11-06

  Compounds of the formula 1 which are useful in disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  式1的化合物在由TNF-α介导的疾病条件中很有用，如类风湿关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和软骨退行性损失。