4-[2-(5-乙基-2-吡啶)乙氧基]苯胺 | 85583-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[2-(5-乙基-2-吡啶)乙氧基]苯胺
• 英文名称: 4-[2-(5-ethylpyridin-2-yl)ethoxy]aniline
• 英文别名: 2-[2-(4-Aminophenoxy)]ethyl-5-ethyl-pyridine；4-[2-(5-ethyl-2-pyridyI)ethoxy]aniline；4-[2-(5-ethyl-2-pyridyl)ethoxy]aniline；pioglitazone amino ether
• CAS: 85583-40-0
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: IDEJJBCHUQNLIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(5-乙基-2-吡啶)乙氧基]苯胺 在 copper(I) oxide 、 盐酸 、 氢溴酸 、 sodium acetate 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 7.33h， 生成 盐酸吡格列酮
  参考文献：
  名称：

  Sohda; Momose; Meguro, Arzneimittel-Forschung/Drug Research, 1990, vol. 40, # 1, p. 37 - 42

  摘要：

  DOI：
• 作为产物：
  描述：

  4-[2-(5-乙基-2-吡啶基)乙氧基]硝基苯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、3.04 MPa 条件下， 以100 %的产率得到4-[2-(5-乙基-2-吡啶)乙氧基]苯胺
  参考文献：
  名称：

  有机硼酸酯与 α-卤代贫电子烯烃的光催化自由基偶联

  摘要：

  在此，我们报告了通过环境友好的无金属催化剂实现的可见光介导的有机硼酸盐与α-卤代贫电子烯烃的加成。该方法适用于各种硼酸衍生物以及烯烃，并以高达 90% 的产率提供相应的饱和 α-卤代衍生物。所得产品是有机合成中的高价值构建模块，可进行各种后续转化。

  DOI：

  10.1021/acs.joc.3c02386

文献信息

• Ether and amide compounds and preparation of thereof as antidiadetics.
  申请人：——

  公开号：US20010008898A1

  公开（公告）日：2001-07-19

  Ether and amide derivatives are disclosed, which are represented by the following formula (I) and its pharmaceutical acceptable salt, and which are useful for the treatment of diabetes. 1 (with the provisos that (i) when A is —O—, then n is 2 or 3 (ii) when A is 2 then n is 1 or 2. R 3 is OH—, CH 3 SO 2 NH—, CF 3 SO 2 NH—, CH 3 SO 2 NHCH 2 —, CF 3 SO 2 NHCH 2 —, HOOC—, CH 3 OOC—, 3 HOOC—CH 2 SO 2 NH—, CF 3 —CH 2 SO 2 NH—, 4 R 8 —NHSO 2 —, R 8 —NHSO 2 —CH 2 —, HOOC—CH 2 —O—, HSO 3 N═CH—, or R 9 —SO 2 NHCO—; R 4 is H, OH, O-alkyl or O—CH 2 OCH 3 ; R 5 is H, halogen atom, —CH 2 COOH or OH; R 6 and R 7 are hydrogen, t-butyl or pyrolidyl; R 8 is hydrogen or lower alkyl; R 9 is alkyl or thienyl; R 10 is lower alkyl) or a pharmaceutically acceptable salt.

  乙醚和酰胺衍生物被披露，其由以下式(I)及其药用可接受盐所代表，并且对于糖尿病的治疗是有用的。 1 （在以下情况下，附加条件为：(i) 当A为—O—时，n为2或3 (ii) 当A为 2 时，n为1或2。R 3 为OH—，CH 3 SO 2 NH—，CF 3 SO 2 NH—，CH 3 SO 2 NHCH 2 —，CF 3 SO 2 NHCH 2 —，HOOC—，CH 3 OOC—， 3 HOOC—CH 2 SO 2 NH—，CF 3 —CH 2 SO 2 NH—， 4 R 8 —NHSO 2 —，R 8 —NHSO 2 —CH 2 —，HOOC—CH 2 —O—，HSO 3 N═CH—，或R 9 —SO 2 NHCO—； R 4 为H，OH，O-烷基或O—CH 2 OCH 3 ； R 5 为H，卤原子，—CH 2 COOH或OH； R 6 和R 7 为氢，叔丁基或吡咯烷基； R 8 为氢或较低烷基； R 9 为烷基或噻吩基； R 10 为较低烷基） 或药用可接受盐。
• [EN] AN IMPROVED PROCESS FOR THE PRODUCTION OF DERIVATIVES OF THIOZOLIDINEDIONES AND THEIR PRECURSORS<br/>[FR] PROCEDE AMELIORE POUR LA PRODUCTION DE DERIVES DE THIOZOLIDINEDIONES ET DE LEURS PRECURSEURS
  申请人：MOREPEN LAB LTD

  公开号：WO2006035459A1

  公开（公告）日：2006-04-06

  The invention provides a process for preparing derivatives of thiozolidinediones and their precursors comprising, (a) reacting a compound of general formula I wherein R1, R2 and R3 may be same or different and represent H, alkyl or alkoxy with C varying from 1 to 6, halogens, mono or di-substituted alkyl and aryl amines, and M represents hydrogen (H) or alkali metal selected from Na, K or Li with a compound of formula II, wherein R4 has the same meaning as R1 or R2 or R3 and X is halogen in presence or absence of solvent(s) under effective conditions to produce nitro ethers of general formula III, where in R1 to R4 has the same meaning as given above, provided when M is H and not its alkali metal salt, an alkali metal salt such as hydroxide or carbonate is required to be added while conducting the said reaction, (b) subjecting the said nitro ethers, with or without isolation, to Raney nickel-catalyzed reduction under conditions effective to produce corresponding nitro aniline ethers (c) coupling the said aniline ether with acrylates under Meerwein arylation conditions in presence of hydrobromic acid to produce α bromo substituted carboxylic acid derivatives followed by subjecting to solvent extractive purification (d) cyclising the purified derivative of α bromo substituted carboxylic acid as obtained in step (c) with thiourea to yield 2-imino -4-thiazolidinones then (e) hydrolyzing the said 2-imino-4-thiazolidinones to produce 2, 4-thiazolidinones and converting the same to its hydrochloride salts as white crystalline solids known to exhibit antidiabetic activity, by conventional methods.

  该发明提供了一种制备噻唑烷二酮及其前体衍生物的过程，包括：(a)将通式I的化合物与通式II的化合物反应，在有效条件下生成通式III的硝基醚，其中R1至R4具有相同的含义，并在M为H而非其碱金属盐时，需要加入羟基或碳酸盐等碱金属盐，(b)将所述硝基醚在Raney镍催化还原条件下还原，生成相应的硝基苯胺醚，(c)在Meerwein芳基化条件下，将所述苯胺醚与丙烯酸酯耦合，在氢溴酸存在下生成α-溴取代的羧酸衍生物，然后经溶剂萃取纯化，(d)将步骤(c)中获得的纯化的α-溴取代的羧酸衍生物与硫脲环化，生成2-亚氨基-4-噻唑烷酮，然后(e)水解所述的2-亚氨基-4-噻唑烷酮，生成2,4-噻唑烷二酮，并通过常规方法将其转化为其盐酸盐，作为白色结晶固体，已知具有抗糖尿病活性。
• [EN] A PROCESS FOR THE PREPARATION OF 4-[2-(5-ETHYL-2-PYRIDYL)ETHOXY]NITROBENZENE AND PIOGLITAZONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 4-[2-(5-ÉTHYL-2-PYRIDYL)ÉTHOXY]NITROBENZÈNE ET DE PIOGLITAZONE
  申请人：ERREGIERRE SPA

  公开号：WO2009133576A1

  公开（公告）日：2009-11-05

  A process for the preparation of 4-[2-(5-ethyl-2-pyridyi)ethoxy]nitrobenzene is described, which comprises the step of reacting 2-(5-ethyl-2-pyridyl)ethanol with 1-fluoro-4-nitrobenzene in acetone in the presence of an alkali metal hydroxide. The intermediate 4-[2-(5-ethyl-2-pyridyI)ethoxy]nitrobenzene is used for the preparation of pioglitazone.

  描述了一种制备4-[2-(5-乙基-2-吡啶基)乙氧基]硝基苯的方法，包括将2-(5-乙基-2-吡啶基)乙醇与1-氟-4-硝基苯在丙酮中在碱性金属氢氧化物存在下反应的步骤。中间体4-[2-(5-乙基-2-吡啶基)乙氧基]硝基苯用于制备吡格列酮。
• [EN] PROCESS FOR THE PREPARATION OF 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL] METHYL]-2,4-THIAZOLIDINEDIONE<br/>[FR] PROCEDE SERVANT A PREPARER 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE
  申请人：SUN PHARMACEUTICAL IND LTD

  公开号：WO2004108721A1

  公开（公告）日：2004-12-16

  A process for the preparation of 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione (formula 1) comprising a. reacting diazonium salt of 4-[2-(5-Ethyl-2-pyridyl) ethoxy] amino- benzene, compound of formula 2, with acrylamide, aqueous HX (wherein X is Br or Cl), under meerwein arylation conditions to yield compound of formula 3; b. condensing compound of formula 3 with thiourea to obtain compound of formula 4; and c. converting compound of formula 4 to compound of formula 1.

  一种制备5-[[4-[2-(5-乙基-2-吡啶基)乙氧基]苯基]甲基]-2,4-噻唑二酮（式1）的方法，包括a.将4-[2-(5-乙基-2-吡啶基)乙氧基]氨基苯的重氮盐（式2化合物）与丙烯酰胺、水溶HX（其中X为Br或Cl）在Meerwein芳基化条件下反应，得到式3化合物；b.将式3化合物与硫脲缩合得到式4化合物；c.将式4化合物转化为式1化合物。
• Pioglitazone impurities
  作者：Richter, Jindrich、Jirman、Havlicek、Hrdina

  DOI：10.1691/ph.2007.8.6720

  日期：——

  Methods of preparation of API pioglitazone were discussed from the point of view of impurities occurrence. Four real impurities (I–IV) of pioglitazone were prepared and characterized by means of NMR spectroscopy.

  从杂质出现的角度讨论了原料药吡格列酮的制备方法。制备了四种真正的吡格列酮杂质（I-IV），并通过核磁共振光谱进行了表征。