3-溴-5-(吡咯烷羰基)吡啶 | 1090388-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-溴-5-(吡咯烷羰基)吡啶
• 中文别名: 3-溴-5-(吡咯烷基羰基)吡啶
• 英文名称: 5-bromo-3-((pyrrolidin-1-yl)methanonyl)pyridine
• 英文别名: 5-bromonicotinic acid pyrrolidinyl amide；(5-Bromopyridin-3-yl)(pyrrolidin-1-yl)methanone；(5-bromopyridin-3-yl)-pyrrolidin-1-ylmethanone
• CAS: 1090388-79-6
• 化学式: C₁₀H₁₁BrN₂O
• mdl: MFCD10000776
• 分子量: 255.114
• InChiKey: JFKJUEBASITIFL-UHFFFAOYSA-N

物化性质

• 沸点：
  377.2±27.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-5-(pyrrolidinocarbonyl)pyridine
Synonyms: (5-Bromopyridin-3-yl)(pyrrolidin-1-yl)methanone

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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-Bromo-5-(pyrrolidinocarbonyl)pyridine
CAS number: 1090388-79-6

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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: C10H11BrN2O
Molecular weight: 255.1

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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, hydrogen bromide.

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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-溴-5-(吡咯烷羰基)吡啶 在 四(三苯基膦)钯 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.5h， 生成 4-(5-((pyrrolidin-1-yl)methanonyl)pyridin-3-yl)-1H-pyrrolo[3,2-c]pyridine
  参考文献：
  名称：

  从麦角灵到吲哚：改进的人类H3受体抑制剂用于发作性睡病的治疗

  摘要：

  麦角灵最近被鉴定为新型的H3受体（H3R）反向激动剂。尽管他们的优化使候选药物在发作性睡病治疗方面具有令人鼓舞的特性，但脑部渗透率仍然很低。为了克服这个问题，麦角灵1（（6a R，9 R，10a R）‐4‐（2‐（二甲基氨基）乙基）‐N‐苯基‐9‐（吡咯烷‐1‐羰基）‐6,6a，8， 9,10,10a-六氢吲哚[4,3- fg ]喹啉-7（4 H）-羧酰胺））被转化为一系列具有高H3R亲和力的吲哚衍生物。通过同时测定它们在小鼠中的脑受体占有率（RO）水平和药效学（PD）效应，对这些新分子进行了分析。这些努力最终导致发现15 m（（R）-1-异丙基-5-（1-（2-（2-甲基吡咯烷酮-1-基）乙基）-1 H吲哚-4-基）吡啶2 （1 H）‐one），其具有理想的特征，显示PD效应与RO有很强的相关性，并且没有可测量的安全系数。通过在大鼠中的脑电图（EEG）测量，证实了其理想的持续时间短。

  DOI：

  10.1002/cmdc.201402418
• 作为产物：
  描述：

  5-溴烟酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-溴-5-(吡咯烷羰基)吡啶
  参考文献：
  名称：

  从麦角灵到吲哚：改进的人类H3受体抑制剂用于发作性睡病的治疗

  摘要：

  麦角灵最近被鉴定为新型的H3受体（H3R）反向激动剂。尽管他们的优化使候选药物在发作性睡病治疗方面具有令人鼓舞的特性，但脑部渗透率仍然很低。为了克服这个问题，麦角灵1（（6a R，9 R，10a R）‐4‐（2‐（二甲基氨基）乙基）‐N‐苯基‐9‐（吡咯烷‐1‐羰基）‐6,6a，8， 9,10,10a-六氢吲哚[4,3- fg ]喹啉-7（4 H）-羧酰胺））被转化为一系列具有高H3R亲和力的吲哚衍生物。通过同时测定它们在小鼠中的脑受体占有率（RO）水平和药效学（PD）效应，对这些新分子进行了分析。这些努力最终导致发现15 m（（R）-1-异丙基-5-（1-（2-（2-甲基吡咯烷酮-1-基）乙基）-1 H吲哚-4-基）吡啶2 （1 H）‐one），其具有理想的特征，显示PD效应与RO有很强的相关性，并且没有可测量的安全系数。通过在大鼠中的脑电图（EEG）测量，证实了其理想的持续时间短。

  DOI：

  10.1002/cmdc.201402418

文献信息

• NEW BICYCLIC DIHYDROISOQUINOLINE-1-ONE DERIVATIVES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20130143863A1

  公开（公告）日：2013-06-06

  The invention provides novel compounds having the general formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A 1 , A 2 , A 3 , A 4 , A 5 and n are as described herein, compositions including the compounds and methods of using the compounds. The compounds are useful, for example, as aldosterone synthase (CYP11B2 or CYP11B1) inhibitors for the treatment or prophylaxis of chronic kidney disease, congestive heart failure, hypertension, primary aldosteronism and Cushing syndrome.

  这项发明提供了具有一般式(I)的新化合物，其中R1、R2、R3、R4、R5、R6、A1、A2、A3、A4、A5和n如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。这些化合物可用作醛固酮合酶（CYP11B2或CYP11B1）抑制剂，用于治疗或预防慢性肾脏疾病、充血性心力衰竭、高血压、原发性醛固酮增多症和库欣综合征。
• Fluorinated aldosterone synthase (CYP11B2)-inhibitors for differential diagnosis between bilateral and unilateral conditions of primary aldosteronism
  作者：Philipp Maier、Britta Heinze、Sabine Gabor、Samario Reese、Stefanie Hahner、Andreas Schirbel

  DOI：10.1016/j.bmcl.2023.129501

  日期：2023.11
• US9133158B2
  申请人：——

  公开号：US9133158B2

  公开（公告）日：2015-09-15
• WO2024086296A1
  申请人：——

  公开号：——

  公开（公告）日：——
• From Ergolines to Indoles: Improved Inhibitors of the Human H3 Receptor for the Treatment of Narcolepsy
  作者：Yves P. Auberson、Thomas Troxler、Xuechun Zhang、Charles R. Yang、Dominik Feuerbach、Yu-Chih Liu、Bharat Lagu、Mark Perrone、Lijun Lei、Xiaoxia Shen、Dushan Zhang、Chunxiu Wang、Tie-Lin Wang、Karin Briner、Mark G. Bock

  DOI：10.1002/cmdc.201402418

  日期：2015.2

  Ergolines were recently identified as a novel class of H3 receptor (H3R) inverse agonists. Although their optimization led to drug candidates with encouraging properties for the treatment of narcolepsy, brain penetration remained low. To overcome this issue, ergoline 1 ((6aR,9R,10aR)‐4‐(2‐(dimethylamino)ethyl)‐N‐phenyl‐9‐(pyrrolidine‐1‐carbonyl)‐6,6a,8,9,10,10a‐hexahydroindolo[4,3‐fg]quinoline‐7(4H)‐carboxamide))

  麦角灵最近被鉴定为新型的H3受体（H3R）反向激动剂。尽管他们的优化使候选药物在发作性睡病治疗方面具有令人鼓舞的特性，但脑部渗透率仍然很低。为了克服这个问题，麦角灵1（（6a R，9 R，10a R）‐4‐（2‐（二甲基氨基）乙基）‐N‐苯基‐9‐（吡咯烷‐1‐羰基）‐6,6a，8， 9,10,10a-六氢吲哚[4,3- fg ]喹啉-7（4 H）-羧酰胺））被转化为一系列具有高H3R亲和力的吲哚衍生物。通过同时测定它们在小鼠中的脑受体占有率（RO）水平和药效学（PD）效应，对这些新分子进行了分析。这些努力最终导致发现15 m（（R）-1-异丙基-5-（1-（2-（2-甲基吡咯烷酮-1-基）乙基）-1 H吲哚-4-基）吡啶2 （1 H）‐one），其具有理想的特征，显示PD效应与RO有很强的相关性，并且没有可测量的安全系数。通过在大鼠中的脑电图（EEG）测量，证实了其理想的持续时间短。