2-溴-6-哌啶基吡啶 | 24255-97-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-溴-6-哌啶基吡啶
• 英文名称: 2-bromo-6-(piperidin-1-yl)pyridine
• 英文别名: 2-bromo-6-piperidin-1-ylpyridine；6'-bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl；6'-bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridyl；6'-Brom-3,4,5,6-tetrahydro-2H-[1,2']bipyridyl；2-bromo-6-piperidinopyridine；2-Brom-6-piperidino-pyridin
• CAS: 24255-97-8
• 化学式: C₁₀H₁₃BrN₂
• 分子量: 241.131
• InChiKey: YHQZMCNKHWPFBS-UHFFFAOYSA-N

物化性质

• 沸点：
  110-112°C/0.1mm
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-6-(piperidin-1-yl)pyridine
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: 2-Bromo-6-(piperidin-1-yl)pyridine
CAS number: 24255-97-8

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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: C10H13BrN2
Molecular weight: 241.1

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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：

  2-溴-6-哌啶基吡啶 在 四(三苯基膦)钯 、 碳酸氢钠 、 一水合肼 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 3-(6-Piperidin-1-ylpyridin-2-yl)aniline
  参考文献：
  名称：

  Diarylureas as Allosteric Modulators of the Cannabinoid CB1 Receptor: Structure–Activity Relationship Studies on 1-(4-Chlorophenyl)-3-{3-[6-(pyrrolidin-1-yl)pyridin-2-yl]phenyl}urea (PSNCBAM-1)

  摘要：

  The recent discovery of allosteric modulators of the CB1 receptor including PSNCBAM-1 (4) has generated significant interest in CB1 receptor allosteric modulation. Here in the first SAR study on 4, we have designed and synthesized a series of analogs focusing on modifications at two positions. Pharmacological evaluation in calcium mobilization and binding assays revealed the importance of alkyl substitution at the 2-aminopyridine moiety and electron deficient aromatic groups at the 4-chlorophenyl position for activity at the CB1 receptor, resulting in several analogs with comparable potency to 4. These compounds increased the specific binding of [H-3]CP55,940, in agreement with previous reports. Importantly, 4 and two analogs dose-dependently reduced the E-max. of the agonist curve in the CB1 calcium mobilization assays, confirming their negative allosteric modulator characteristics. Given the side effects associated with CB1 receptor orthosteric antagonists, negative allosteric modulators provide an alternative approach to modulate the pharmacologically important CB1 receptor.

  DOI：

  10.1021/jm501042u
• 作为产物：
  描述：

  哌啶 、 2,6-二溴吡啶 在 potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以98%的产率得到2-溴-6-哌啶基吡啶
  参考文献：
  名称：

  获得2-氨基吡啶–具有重要生物和化学意义的化合物

  摘要：

  2-氨基吡啶是生物活性天然产物，重要医学化合物和有机材料的关键结构核心，因此，它们是非常有价值的合成靶标。少数报道的6-取代的2-氨基吡啶和缺乏灵活，有效和通用的合成方法表明了对制备其新方法的迫切需要。2,6-二溴吡啶和伯或仲的，环状或无环的，以及脂族或芳族胺之间的反应进行了示出，以选择性地得到相应的6-溴吡啶-2-胺在非常高的产率，其被成功地用作今后的C基板 Ç交叉偶联反应。最近推出的二氯双[1-（二环己基膦酰基）哌啶]钯（1）用作6-溴吡啶-2-胺与芳基硼酸，二芳基和二烷基锌试剂或烯烃的交叉偶联催化剂，因此，也是此类底物的出色的CC交叉偶联催化剂。而且，所提出的所有反应方案均在均匀应用的每种催化剂中使用。胺化反应和交叉偶联反应的范围都得到了很好的定义，可以使反应方案直接直接适用于其他胺和/或偶联伙伴，因此首次提供了非常灵活且普遍适用的反应方案获得2-氨基吡啶。

  DOI：

  10.1002/adsc.201000942

文献信息

• [EN] CYCLIC INHIBITORS OF 11ß-HYDROXYSTERIOD DEHYDROGENASE 1<br/>[FR] INHIBITEURS CYCLIQUES DE LA 11?-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE 1
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2009017664A1

  公开（公告）日：2009-02-05

  This invention relates to novel compounds of the Formula (I), (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih); (Ii); (Ij), (Ik), (II) pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11 β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.

  本发明涉及式(I)、(Ia)、(Ib)、(Ic)、(Id)、(Ie)、(If)、(Ig)、(Ih)；(Ii)；(Ij)，(Ik)，(II)的新颖化合物，其药用可接受的盐以及药物组合物，这些化合物对于治疗与调节或抑制哺乳动物中的11β-HSD1相关的疾病是有用的。本发明进一步涉及新颖化合物的药物组合物及其在减少或控制细胞中皮质醇的产生或抑制细胞中将可的松转化为皮质醇的方法。
• Transition metal-free amination of aryl halides—A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1016/j.tet.2008.11.072

  日期：2009.2

  intermediates is not necessary, allowing the synthesis of pyridine-2,6-diamines in ‘one-pot’. However, catalysts are in many cases not required to efficiently and selectively couple aryl halides with amines, making transition metal-free versions of the Buchwald–Hartwig reaction extremely attractive for the synthesis of N-arylated amines with substrates containing substituents on the aryl halide, which either promote

  提出了一种简单，可靠的反应方案，用于在无过渡金属的反应条件下，由芳基卤化物与各种（也是位阻的）胺反应衍生而来的各种N-芳基化胺的清洁，快速和高产率合成。二恶烷和KN（Si（CH 3）3）2被发现是该转化的理想溶剂和基础。观察到的转化率和产率极好，并且在大多数反应中进行的反应明显高于其催化形式的反应。此外，几乎可以选择性合成6-卤代吡啶-2-胺和不对称吡啶-2,6-二胺（分别来自2,6-二溴吡啶和2,6-二氯吡啶的连续反应）。在非常短的反应时间内即可获得定量收率（相对于2,6-二卤代吡啶）。不需要纯化6-卤代吡啶-2-胺中间体，从而可以在“一锅法”中合成吡啶-2,6-二胺。但是，催化剂在许多情况下不是有效地和选择性地使芳基卤化物与胺偶联，使无过渡金属形式的Buchwald-Hartwig反应对于合成N-芳基化胺（在芳基卤化物上具有取代基的底物）极具吸引力，这会促进区域选择性和/或不需要区域选择性胺化。
• Palladium-Catalyzed Selective Amination of Haloaromatics on KF-Alumina Surface
  作者：Basudeb Basu、Pralay Das、Ashish Nanda、Sajal Das、Sajal Sarkar

  DOI：10.1055/s-2005-865241

  日期：——

  An efficient palladium-catalyzed amination, including polyaminations of aromatic bromides mediated on a surface of KF-alumina, is reported. The solvent-free one-pot protocol avoids the use of a strong base (sodium tert-butoxide) making it applicable to substrates containing a base-sensitive functional group. It proceeds without concomitant reductive bromination and provides access to selective amination of polyhaloaromatics.

  报道了一种高效的钯催化胺化反应，包括在KF-氧化铝表面介导的芳香溴化物的多胺化反应。该无溶剂一步法方案避免了强碱（叔丁醇钠）的使用，使其适用于含有碱敏感官能团的底物。该反应无需伴随还原性溴化作用，能够实现对多卤代芳香化合物的高选择性胺化反应。
• [EN] SUBSTITUTED OCTAHYDROPYRROLO[1,2-A]PYRAZINE SULFONAMIDES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] OCTAHYDROPYRROLO[1,2-A]PYRAZINE SULFONAMIDES SUBSTITUÉS À TITRE D'INHIBITEURS DES CANAUX CALCIQUES
  申请人：ABBVIE INC

  公开号：WO2013049174A1

  公开（公告）日：2013-04-04

  The present application relates to: (a) compounds of Formula (I): (I), and salts thereof, wherein Z', Z", L2, G2, R1, and R2 are as defined in the specification; (b) compositions comprising such compounds and salts; and (c) methods of use of such compounds, salts, and compositions, particularly use as calcium channel blockers.

  本申请涉及：(a) 公式(I)的化合物及其盐，其中Z'、Z"、L2、G2、R1和R2如规范中所定义；(b) 包含这些化合物和盐的组合物；以及(c) 使用这些化合物、盐和组合物的方法，特别是用作钙通道阻滞剂。
• [EN] BENZENE OR THIOPHENE DERIVATIVE AND USE THEREOF AS VAP-1 INHIBITOR<br/>[FR] DÉRIVÉ DE BENZÈNE OU DE THIOPHÈNE ET SON UTILISATION EN TANT QU'INHIBITEUR DE LA VAP-1
  申请人：R TECH UENO LTD

  公开号：WO2009145360A1

  公开（公告）日：2009-12-03

  The present invention provides a novel benzene derivative or thiophene derivative useful as a VAP-1 inhibitor, or a medicament for the prophylaxis or treatment of a VAP-1 associated disease and the like, namely, a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种新颖的苯衍生物或噻吩衍生物，可用作VAP-1抑制剂，或用作预防或治疗与VAP-1相关的疾病等的药物，即由以下式（I）表示的化合物：其中每个符号如本说明书中所定义，或其药学上可接受的盐。