盐酸比格列酮杂质25 | 144809-26-7

• 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: 盐酸比格列酮杂质25
• 中文别名: 2-(5-乙基吡啶-2-基)乙基甲基磺酸盐
• 英文名称: 2-(5-ethyl-pyridin-2-yl)ethyl methanesulfonate
• 英文别名: 2-(5-ethyl-2-pyridyl)ethyl methanesulfonate；2-ethylpyridin-5-ylethyl mesylate；2-(5-ethylpyridin-2-yl)ethyl methanesulphonate；2-(5-ethylpyridine-2-yl)-ethyl methanesulfonate；methanesulfonic acid 2-(5-ethyl-pyridin-2-yl)-ethyl ester；(5-ethyl-2-pyridyl)ethyl methanesulfonate；2-(5-ethylpyridin-2-yl)ethyl methanesulfonate
• CAS: 144809-26-7
• 化学式: C₁₀H₁₅NO₃S
• 分子量: 229.3
• InChiKey: QBBOABZXKOJOEC-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±30.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  盐酸比格列酮杂质25 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-2-fluorobenzenamine
  参考文献：
  名称：

  Synthesis andIn VitroAntimicrobial Screening of New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol

  摘要：

  A new series of azetidinones is described in this paper; Schiff base (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o) were synthesized from 4‐[2‐(5‐ethylpyridin‐2‐yl)ethoxy]benzaldehyde, which was used to synthesize azetidinones (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o), (6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j, 6k, 6l, 6m, 6n, 6o), and (7a, 7b, 7c, 7d, 7e, 7f, 7g, 7h, 7i, 7j, 7k, 7l, 7m, 7n, 7o). The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H NMR, and 13C NMR spectral data. All the products were screened against different strains of bacteria and fungi. Most of the monosubstituted and disubstituted chloro groups are more effective to both bacterial and fungal species in comparison with the standard drugs.

  DOI：

  10.1002/jhet.1734
• 作为产物：
  描述：

  5-乙基-2-吡啶乙醇 生成 盐酸比格列酮杂质25
  参考文献：
  名称：

  Org. Process. Res. Dev. 2009, 13, 1190-1194

  摘要：

  DOI：

文献信息

• [EN] ENANTIOMERIC RESOLUTION METHOD<br/>[FR] PROCÉDÉ DE RÉSOLUTION ÉNANTIOMÉRIQUE
  申请人：PULMAGEN THERAPEUTICS INFLAMMATION LTD

  公开号：WO2011015868A1

  公开（公告）日：2011-02-10

  A method for the preparation of pioglitazone O,O'-dibenzoyl-L-tartrate wherein the content by weight of pioglitazone consists of at least 95 % by weight of the 5R enantiomer and less than 5 % of the 5S enantiomer, which method comprises: (1a) adding seed crystals of 5R- pioglitazone O,O'-dibenzoyl-l-tartrate to a rnethanol-water solution of racemic pioglitazone hydrochloride and O,O'-dibenzoyI-L-tartaric acid, thereby precipitating pioglitazone O,O'- dibenzoyl-L-tartrate;(1b) recovering said precipitate from step (1a); (1c) forming a solution of the precipitate from step (1b) in a solvent mixture of methanol, acid and water and mixing into to the resultant solution seed crystals of 5R-pioglitazone O,O'-dibenzoyl-L-tartrate, thereby precipitating pioglitazone O,O'-dibenzoyl-L-tartrate; (1d) recovering said precipitate from step (1c); (1e) repeating steps (1c) and (1d), the recovered product being the desired pioglitazone O,O'-dibenzoy! tartrate wherein the content by weight of pioglitazone consists of at least 95 % by weight of the 5R enantiomer and less than 5 % of the 5S enantiomer. Also disclosed is a modification of the method in which step 1(e) is omitted.

  一种制备吡格列酮O，O'-双苯甲酰-L-酒石酸盐的方法，其中吡格列酮的重量含量至少为其5R对映体的95%重量，5S对映体的含量少于5%，该方法包括：（1a）将5R-吡格列酮O，O'-双苯甲酰-L-酒石酸晶种加入到外消旋吡格列酮盐酸盐和O，O'-双苯甲酰-L-酒石酸的甲醇-水溶液中，从而沉淀吡格列酮O，O'-双苯甲酰-L-酒石酸盐；（1b）从步骤（1a）中回收所述沉淀物；（1c）在甲醇、酸和水的溶剂混合物中形成步骤（1b）中的沉淀物的溶液，并将5R-吡格列酮O，O'-双苯甲酰-L-酒石酸晶种混入到所得溶液中，从而沉淀吡格列酮O，O'-双苯甲酰-L-酒石酸盐；（1d）从步骤（1c）中回收所述沉淀物；（1e）重复步骤（1c）和（1d），回收的产品即为所需的吡格列酮O，O'-双苯甲酰-L-酒石酸盐，其中吡格列酮的重量含量至少为其5R对映体的95%重量，5S对映体的含量少于5%。还揭示了一种修改该方法的步骤，其中省略了步骤1（e）。
• [EN] PROCESSES FOR MAKING THIAZOLIDINEDIONE DERIVATIVES AND COMPOUNDS THEREOF<br/>[FR] PROCEDES DE FABRICATION DE DERIVES DE THIAZOLIDINEDIONE ET COMPOSES ASSOCIES
  申请人：SYNTHON BV

  公开号：WO2004101560A1

  公开（公告）日：2004-11-25

  A compound of the formula (I): wherein A represents a ring group connected to the oxygen atom by a C1 to C6 hydrocarbon chain, R is hydrogen or a C1-C4 alkyl, and Q is hydrogen, or an amine protecting group such as acetyl, trifluoroacetyl, benzoyl, benzyl, or trityl, is useful in making thiazolidinedione derivatives (formula (II)), such as pioglitazone, rosiglitazone and troglitazone.

  公式（I）的化合物：其中A代表通过碳1至碳6烃链连接到氧原子的环基团，R是氢或C1-C4烷基，Q是氢，或者是一种胺保护基团，如乙酰基、三氟乙酰基、苯甲酰基、苄基或三苄基，可用于制备噻唑烷二酮衍生物（公式（II）），如派格列酮、罗格列酮和曲格列酮。
• Design and synthesis of new imidazolinone derivatives as potential antifungal agents
  作者：Navin B. Patel、Hemant R. Patel

  DOI：10.1002/jhet.588

  日期：2011.3

  6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j, 6k, 6l, 6m, 6n, 6o) were synthesized from the reaction of pyrimidine and oxazolone derivatives (prepared by Erlenmeyer azlactone synthesis). The structures of the synthesized compounds were assigned on the basis of elemental analyses, IR, 1H‐NMR, and 13C‐NMR spectral data. All the products were screened against different strains of bacteria and fungi. Most of these compounds

  描述了一系列新的查耳酮，嘧啶和咪唑啉酮。查耳酮（4a，4b，4c，4d，4e，4f，4g，4h，4i，4j，4k，4l，4m，4n，4o）是由铅4 [2-（5-乙基吡啶-2--2-基）制成的乙氧基]苯甲醛。嘧啶类（5a，5b，5c，5d，5e，5f，5g，5h，5I，5J，5K，5升，5米，5N，50）是从查尔酮在碱介质中的反应和硝酸胍制备。咪唑啉酮（6a，6b，6c，6d，6e，6f，6g，6h，6i，6j，6k，6l，6m，6n，6o由嘧啶和恶唑酮衍生物的反应（由Erlenmeyer氮杂内酯合成制备）合成。根据元素分析，IR，1 H-NMR和13 C-NMR光谱数据指定合成化合物的结构。对所有产品进行了针对不同菌株的细菌和真菌的筛选。与标准药物相比，这些化合物大多数显示出更好的抑制活性。J.杂环化​​学。（2011）。
• Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)₂
  作者：Aiyou Xia、Peizhuo Lv、Xin Xie、Yuanhong Liu

  DOI：10.1021/acs.orglett.0c02722

  日期：2020.10.16

  Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate

  已经开发了用镍催化的Zn（CN）2氰化未活化的伯和仲烷基甲磺酸酯。该反应提供了一种合成烷基腈的有效途径，该烷基腈具有广泛的底物范围，良好的官能团耐受性以及与杂环化合物的相容性。机理研究表明，原位生成的烷基碘是反应性中间体，烷基碘的逐步释放对于反应的成功至关重要。
• [EN] PROCESS FOR THE SYNTHESIS OF PIOGLITAZONE HYDROGEN CHLORIDE<br/>[FR] PROCEDE DE SYNTHESE DE CHLORURE D'HYDROGENE DE PIOGLITAZONE
  申请人：RICHTER GEDEON VEGYESZET

  公开号：WO2005058827A1

  公开（公告）日：2005-06-30

  The invention relates to a process for the synthesis of pioglitazone hydrogen chloride - which is an antidiabetic drug - via novel intermediates by reacting 4-[2-(5-ethyl-2-pyridinyl)-ethoxy]-benzaldehyde salt of formula (II), wherein HX is: HCI, CF3COOH, C4H4O4, (COOH)2 with a base and then thiazolidine-2,4-dione, and the obtained 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-2,4-thiazolidinedione base is treated with hydrochloric acid and the obtained 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl] methylene]-2,4-tiazolidinedione hydrogen chloride of formula(III) is hydrogenated in the presence of a catalyst. Further objects of the invention are the salts of general formula (II) and the benzylidene derivative of formula (III).

  该发明涉及一种合成吡格列酮盐酸盐的过程-这是一种抗糖尿病药物-通过用碱与4-[2-(5-乙基-2-吡啶基)-乙氧基]-苯甲醛盐（式（II））的HX反应，其中HX为：HCl，CF3COOH，C4H4O4，（COOH）2，然后与噻唑烷-2,4-二酮反应，得到5-[[4-[2-(5-乙基-2-吡啶基)乙氧基]苯基]亚甲基]-2,4-噻唑烷二酮碱，然后用盐酸处理，得到5-[[4-[2-(5-乙基-2-吡啶基)乙氧基]苯基]亚甲基]-2,4-噻唑烷二酮盐酸盐（式（III）），在催化剂存在下，对其进行氢化。该发明的进一步对象是通式（II）的盐和通式（III）的苄亚甲基衍生物。