N-(5-甲基-2-吡嗪基)氨基甲酸苄酯 | 1033418-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(5-甲基-2-吡嗪基)氨基甲酸苄酯
• 中文别名: 2-(Cbz-氨基)-5-甲基吡嗪
• 英文名称: benzyl-5-methylpyrazin-2-yl carbamate
• 英文别名: Benzyl (5-methylpyrazin-2-yl)carbamate；benzyl N-(5-methylpyrazin-2-yl)carbamate
• CAS: 1033418-57-3
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: DYKSQZLJHRCKSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  4

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: 2-(Cbz-Amino)-5-methylpyrazine
Synonyms: Benzyl 5-methylpyrazin-2-ylcarbamate, 2-(Benzyloxycarbonylamino)-5-methylpyrazine

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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-(Cbz-Amino)-5-methylpyrazine
CAS number: 1033418-57-3

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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: C13H13N3O2
Molecular weight: 243.3

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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：

  N-(5-甲基-2-吡嗪基)氨基甲酸苄酯 在 5%-palladium/activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以89.6%的产率得到2-氨基-5-甲基吡嗪
  参考文献：
  名称：

  使用Curtius重排作为吡嗪构建基团的多千克生产的一部分

  摘要：

  葡萄糖激酶激活剂的商业路线定义要求重新评估用于获取多千克量的2-氨基-5-甲基吡嗪的合成和工艺。在考虑了不同的选择之后，选择了用于药物化学路线的库尔修斯重排的变化形式，以进行进一步的开发。库尔修斯重排的酰基叠氮化物的形成需要采取过程安全控制策略。从5-甲基吡嗪-2-羧酸开始，开发的工艺用于成功交付总重量达68％的多千克量的2-氨基-5-甲基吡嗪。

  DOI：

  10.1021/acs.oprd.7b00340
• 作为产物：
  描述：

  5-甲基吡嗪-2-羧酸 在 叠氮磷酸二苯酯 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 N-(5-甲基-2-吡嗪基)氨基甲酸苄酯
  参考文献：
  名称：

  使用Curtius重排作为吡嗪构建基团的多千克生产的一部分

  摘要：

  葡萄糖激酶激活剂的商业路线定义要求重新评估用于获取多千克量的2-氨基-5-甲基吡嗪的合成和工艺。在考虑了不同的选择之后，选择了用于药物化学路线的库尔修斯重排的变化形式，以进行进一步的开发。库尔修斯重排的酰基叠氮化物的形成需要采取过程安全控制策略。从5-甲基吡嗪-2-羧酸开始，开发的工艺用于成功交付总重量达68％的多千克量的2-氨基-5-甲基吡嗪。

  DOI：

  10.1021/acs.oprd.7b00340

文献信息

• CHEMICAL PROCESS 632
  申请人：Butters Michael

  公开号：US20100210841A1

  公开（公告）日：2010-08-19

  A process for preparing pharmaceutically active compounds of formula (I) or a salt thereof wherein R 1 , n, m, R 3 , R 6 , X 1 , X 2 , X 3 and X 4 are as defined in the specification, is described. Novel intermediates are also described and claimed.

  提供制备具有以下结构的药用活性化合物（I）或其盐的方法 其中R1、n、m、R3、R6、X1、X2、X3和X4如规范中所定义。还描述和声明了新颖的中间体。
• CRYSTALLINE POLYMORPHIC FORM 631
  申请人：BOWDEN Sharon Ann

  公开号：US20100210621A1

  公开（公告）日：2010-08-19

  A new polymorphic form of 3-[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide, processes for making it and its use as an activator of glucokinase are described.

  描述了一种新的多形态形式的3-[5-(氮杂环丙酰基)吡嗪-2-基]氧基}-5-[(1S)-1-甲基-2-(甲氧基)乙基]氧基}-N-(5-甲基吡嗪-2-基)苯甲酰胺，以及制备该化合物的方法和其作为葡萄糖激酶激活剂的用途。
• A modular flow reactor for performing Curtius rearrangements as a continuous flow process
  作者：Marcus Baumann、Ian R. Baxendale、Steven V. Ley、Nikzad Nikbin、Christopher D. Smith、Jason P. Tierney

  DOI：10.1039/b801631n

  日期：——

  The use of a mesofluidic flow reactor is described for performing Curtius rearrangement reactions of carboxylic acids in the presence of diphenylphosphoryl azide and trapping of the intermediate isocyanates with various nucleophiles.

  描述了使用中流体流动反应器在二苯基磷酰基叠氮化物存在下进行羧酸的库尔修斯重排反应并用各种亲核试剂捕集中间异氰酸酯。
• Chemical process 632
  申请人：AstraZeneca AB

  公开号：US08076481B2

  公开（公告）日：2011-12-13

  A process for preparing pharmaceutically active compounds of formula (I) or a salt thereof wherein R1, n, m, R3, R6, X1, X2, X3 and X4 are as defined in the specification, is described. Novel intermediates are also described and claimed.

  本发明揭示了一种制备公式（I）的药物活性化合物或其盐的方法，其中R1、n、m、R3、R6、X1、X2、X3和X4如规范中定义。同时，还描述和声明了新的中间体。
• Crystalline polymorphic form of glucokinase activator
  申请人：AstraZeneca AB

  公开号：US08093252B2

  公开（公告）日：2012-01-10

  A new polymorphic form of 3-[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide, processes for making it and its use as an activator of glucokinase are described.

  本文描述了一种新的多态形式的3-[5-(氮杂四环-1-基甲酰)吡嗪-2-基]氧基}-5-[(1S)-1-甲基-2-(甲氧基)乙基]氧基}-N-(5-甲基吡嗪-2-基)苯甲酰胺，制备它的工艺以及它作为葡萄糖激酶激活剂的用途。