pyridin-3-yl-thiazol-2-yl-amine | 58061-59-9

• 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
• 英文名称: pyridin-3-yl-thiazol-2-yl-amine
• 英文别名: 2-Pyridyl-(3)-aminothiazol；N-pyridin-3-yl-1,3-thiazol-2-amine
• CAS: 58061-59-9
• 化学式: C₈H₇N₃S
• 分子量: 177.23
• InChiKey: AJBFCQRZTQCXLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyridin-3-yl-thiazol-2-yl-amine 在 溴 、 溶剂黄146 作用下， 生成 (5-bromo-thiazol-2-yl)-pyridin-3-yl-amine
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

  摘要：

  A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity, and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.060
• 作为产物：
  描述：

  N-(pyridin-3-ylcarbamothioyl)benzamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 pyridin-3-yl-thiazol-2-yl-amine
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

  摘要：

  A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity, and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.060

文献信息

• General cross-coupling reactions with adaptive dynamic homogeneous catalysis
  作者：Indrajit Ghosh、Nikita Shlapakov、Tobias A. Karl、Jonas Düker、Maksim Nikitin、Julia V. Burykina、Valentine P. Ananikov、Burkhard König

  DOI：10.1038/s41586-023-06087-4

  日期：——

  (AD-HoC) with nickel under visible-light-driven redox reaction conditions for general C(sp2)–(hetero)atom coupling reactions. The self-adjustive nature of the catalytic system allowed the simple classification of dozens of various classes of nucleophiles in cross-coupling reactions. This is synthetically demonstrated in nine different bond-forming reactions (in this case, C(sp2)–S, Se, N, P, B, O, C(sp3, sp2

  交叉偶联反应是现代有机合成中最重要的转化之一1,2,3。尽管考虑到各种方案，报道的（杂）芳基卤化物和亲核试剂偶联配偶体的范围非常大，但化合物类别之间的反应条件差异很大，因此需要根据具体情况重新优化反应条件4。在这里，我们介绍了在可见光驱动的氧化还原反应条件下镍的自适应动态均相催化（AD-HoC），用于一般的 C( sp 2 )–(杂)原子偶联反应。催化系统的自我调节性质允许在交叉偶联反应中对数十种不同类别的亲核试剂进行简单分类。这在九种不同的成键反应（在本例中为 C( sp 2 )–S、Se、N、P、B、O、C( sp 3、  sp 2、  sp )、Si、Cl）中得到了综合证明在可预测的反应条件下进行数百个合成实例。催化反应中心和条件因添加的亲核试剂或如果需要而添加市售的廉价胺碱而彼此不同。
• A General C–N Cross-Coupling to Synthesize Heteroaryl Amines Using a Palladacyclic N-Heterocyclic Carbene Precatalyst
  作者：Ruoqian Fan、Meiying Kuai、Dong Lin、Felix Bauer、Weiwei Fang

  DOI：10.1021/acs.orglett.2c03580

  日期：2022.12.2

  6-diisopropylphenyl)acenaphthoimidazol-2-ylidene (AnIPr) with an achiral 2-naphthyl-4,4-dimethyloxazoline palladacyclic fragment. Applying this precatalyst enabled a general protocol for Pd-catalyzed C–N cross-coupling reactions of challenging five- or six-membered ring heteroaryl chlorides and various heterocyclic amines. The desired aminated products, including commercial pharmaceuticals or key intermediates such

  通过将 1,3-双(2,6-二异丙基苯基)苊并咪唑-2-亚基 (AnIPr) 与非手性 2-萘基-4,4-二甲基恶唑啉钯环片段结合，设计了一种新型钯环 N-杂环卡宾预催化剂。应用这种预催化剂可以实现具有挑战性的五元或六元环杂芳基氯和各种杂环胺的 Pd 催化 C-N 交叉偶联反应的通用方案。理想的胺化产品，包括商业药物或关键中间体，如吡贝地尔、嘧菌环胺、V600E BRAF 抑制剂、曲苯那敏、517-β-羟基类固醇脱氢酶抑制剂、brexpipRAzole 和 sonidegib，实现了良好至优异的收率（>61 例，≤99 % 产量）。
• A General Catalyst for Buchwald-Hartwig Amination to Prepare Secondary Five-Membered Heteroaryl Amines with Breaking the Base Barrier
  作者：Fabin Zhou、Lixue Zhang、Wenbo Hu、Bingxin Yuan、Ji-cheng Shi

  DOI：10.1016/j.jcat.2023.02.018

  日期：2023.3

  sometimes needing strong bases, perplexes the application of the palladium-catalyzed CN cross-coupling reactions. The terphenyl phosphine TXPhos supporting palladium catalyst [(TXPhos)(allyl)PdCl] dramatically broadened the existing scope of five-membered heteroaryl substrates and made the weak bases KHCO3 and KOAc become general and optimal choices. Therefore, the barrier of bases has been broken and

  底物的范围限制，特别是五元杂芳基底物通常出现在医学和生物活性分子中，以及高钯负载量和有时需要强碱，困扰着钯催化的 C N 交叉偶联反应的应用。三联苯基膦TXPhos负载钯催化剂[(TXPhos)(allyl)PdCl]大大拓宽了五元杂芳基底物的现有范围，使弱碱KHCO 3 和KOAc成为通用和优化的选择。因此，碱基屏障已被打破，并建立了通​​过钯催化的 C N 交叉偶联反应制备仲五元杂芳基胺的有吸引力的方案。
• Buchwald‐Hartwig Amination of Coordinating Heterocycles Enabled by Large‐but‐Flexible Pd‐BIAN‐NHC Catalysts**
  作者：Dong‐Hui Li、Xiao‐Bing Lan、A‐Xiang Song、Md. Mahbubur Rahman、Chang Xu、Fei‐Dong Huang、Roman Szostak、Michal Szostak、Feng‐Shou Liu

  DOI：10.1002/chem.202103341

  日期：2022.1.19

  AbstractA new class of large‐but‐flexible Pd‐BIAN‐NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N‐heterocyclic carbene) has been rationally designed to enable the challenging Buchwald‐Hartwig amination of coordinating heterocycles. This robust class of BIAN‐NHC catalysts permits cross‐coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron‐deficient heterocycles containing multiple heteroatoms with BIAN‐INon (N,N′‐bis(2,6‐di(4‐heptyl)phenyl)‐7H‐acenaphtho[1,2‐d]imidazol‐8‐ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN‐NHC scaffold.
• Boedeker,J. et al., Journal fur praktische Chemie (Leipzig 1954), 1975, vol. 317, p. 953 - 958
  作者：Boedeker,J. et al.

  DOI：——

  日期：——