5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole | 409098-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
• 英文别名: (5-difluoromethoxy)-2-[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl-1H-benzimidazole；2-(4-chloro-3-methoxypyrid-2-yl)methanesulfinyl-5-difluoromethoxy-1H-benzimidazole；2-(4-chloro-3-methoxypyrid-2-ylmethanesulfinyl)-5-difluoromethoxy-1H-benzimidazole；2-{[(4-Chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl}-6-(difluorom ethoxy)-1H-benzimidazole；2-[(4-chloro-3-methoxypyridin-2-yl)methylsulfinyl]-6-(difluoromethoxy)-1H-benzimidazole
• CAS: 409098-86-8
• 化学式: C₁₅H₁₂ClF₂N₃O₃S
• 分子量: 387.794
• InChiKey: MZYFONHFAIZFRU-UHFFFAOYSA-N

物化性质

• 沸点：
  585.4±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以70.8%的产率得到pantoprazole sodium
  参考文献：
  名称：

  Process for the preparation of pantoprazole and salts thereof

  摘要：

  一种制备泮托拉唑及其盐的方法，包括将巯基咪唑与哌啶反应，得到2-吡啶基-甲基磺酰基-2-苯并咪唑中间体，然后用ε-邻苯二甲酰亚巨环酸进行氧化，最后进行甲氧基化。

  公开号：

  US20050096352A1
• 作为产物：
  描述：

  5-(二氟甲氧基)-2-{[(4-氯-3-甲氧基-2-吡啶基)甲基]硫}-1氢-苯并咪唑 以83.5的产率得到5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
  参考文献：
  名称：

  [EN] A PROCESS FOR THE PREPARATION OF PANTOPRAZOLE AND INTERMEDIATES THEREFOR
  [FR] PROCEDE DE PREPARATION DE PANTOPRAZOLE ET DE PRODUITS INTERMEDIAIRES DE CELUI-CI

  摘要：

  本文描述了一种基于新型中间化合物的活性成分泮托拉唑的制备方法，该中间化合物的通用式为(I)，其中X为卤素原子，n=0或1，当n=1时，中间化合物为甲氧基化，当n=0时，所述中间化合物首先被氧化为n=1，然后再被甲氧基化。同时还描述了这些新型中间体以及其制备方法。

  公开号：

  WO2002028852A1

文献信息

• Process for the preparation of organic compounds containing a sulfinyl or sulfonyl group
  申请人：DINAMITE DIPHARMA S.P.A. abbreviated DIPHARMA S.P.A.

  公开号：US20040192929A1

  公开（公告）日：2004-09-30

  A process for the oxidation of thioethers to sulfoxides or sulfones or for the oxidation of sulfoxides to sulfones by treatment of thioethers or sulfoxides with an oxidizing amount of &egr;-phthalimidoperhexanoic acid is particularly useful for the preparation of compounds of industrial interest, in particular pharmaceuticals for human or veterinary use.

  一种将硫醚氧化为亚砜或砜，或将亚砜氧化为砜的过程，通过用适量的ε-邻苯二甲酰亚丙基己酸处理硫醚或亚砜，特别适用于制备工业感兴趣的化合物，特别是用于人类或兽医用途的药物。
• Process for the preparation of pyridine-methylsulfinyl compounds
  申请人：ALLEGRINI Pietro

  公开号：US20090076277A1

  公开（公告）日：2009-03-19

  A process for the preparation of a compound of formula (I), or a salt thereof, wherein Q is ═CR 8 — or ═N—; and R 1 -R 8 are as herein defined; comprising the reaction of a compound of formula (II), or a salt thereof, wherein Q, R 1 -R 7 are as herein defined; with a reducing agent selected from a trivalent phosphorous compound, an oxidizable solvent and a sulfonic acid chloride; and, if desired, the conversion of a compound of formula (I) to another compound of formula (I) or a salt thereof.

  一种制备式（I）化合物或其盐的方法，其中Q为═CR8—或═N—; R1-R8如本文所定义; 包括将式（II）化合物或其盐，其中Q，R1-R7如本文所定义；与三价磷化合物、可氧化溶剂和磺酸氯选择的还原剂反应；如果需要，将式（I）化合物转化为另一种式（I）化合物或其盐。
• PROCESS FOR THE PREPARATION OF PYRIDINE COMPOUNDS
  申请人：ALLEGRINI Pietro

  公开号：US20070249662A1

  公开（公告）日：2007-10-25

  A process for preparation of a compound of formula (I), both as the isomeric mixture and individual isomers, wherein Q is ═CR 8 — or ═N—; each R 1 , R 2 , R 3 , R 4 is independently selected from hydrogen, halogen, hydroxy; nitro; C 1 -C 6 alkyl optionally substituted with hydroxy; alkylthio C 1 -C 6 ; C 1 -C 6 alkoxy optionally substituted with halogen or C 1 -C 6 alkoxy; phenyl-C 1 -C 6 alkyl; phenyl-C 1 -C 6 alkoxy; and —N(RaRb) wherein each Ra and Rb is independently hydrogen or C 1 -C 6 alkyl or Ra and Rb, taken together with the nitrogen atom they are linked to, form a saturated heterocyclic ring; and each R 5 , R 6 , R 7 , R 8 is independently selected from hydrogen, halogen, hydroxy; C1-C6 alkyl optionally substituted with hydroxy; alkylthio C 1 -C 6 ; C 1 -C 6 alkoxy optionally substituted with halogen; C 1 -C 6 alkyl-carbonyl, C 1 -C 6 alkoxy-carbonyl, and oxazol-2-yl; comprising converting a compound of formula (IV), to said compound of formula (I), in the presence of a catalyst, if necessary in an organic solvent.

  一种制备式(I)化合物的方法，包括其同分异构体混合物和单个异构体，其中Q为═CR8—或═N—；每个R1、R2、R3、R4独立选择自氢、卤素、羟基、硝基、C1-C6烷基（可选用羟基取代）、C1-C6烷基硫醇、C1-C6烷氧基（可选用卤素或C1-C6烷氧基取代）、苯基-C1-C6烷基、苯基-C1-C6烷氧基和—N(RaRb)（其中每个Ra和Rb独立选择自氢或C1-C6烷基，或Ra和Rb连同它们链接到的氮原子形成饱和杂环环）；每个R5、R6、R7、R8独立选择自氢、卤素、羟基、C1-C6烷基（可选用羟基取代）、C1-C6烷基硫醇、C1-C6烷氧基（可选用卤素取代）、C1-C6烷基-羰基、C1-C6烷氧基-羰基和噁唑-2-基；包括在有机溶剂中，在催化剂的存在下，将式(IV)化合物转化为所述式(I)化合物，必要时使用催化剂。
• A process for the preparation of pyridine compounds
  申请人：Dipharma Francis S.r.l.

  公开号：EP1847538A1

  公开（公告）日：2007-10-24

  A process for the preparation of a compound of formula (I) or a salt thereof, both as the isomeric mixture and the individual isomers, wherein Q is =CR8- or =N-; each R1, R2, R3 and R4 is independently selected from hydrogen, halogen, hydroxy; nitro; C1-C6 alkyl optionally substituted with hydroxy; alkylthio C1-C6; C1-C6 alkoxy optionally substituted with halogen or C1-C6 alkoxy; phenyl-C1-C6 alkyl; phenyl-C1-C6 alkoxy; and - N(RaRb) wherein each Ra and Rb is independently hydrogen or C1-C6 alkyl or Ra and Rb, taken together with the nitrogen atom they are linked to, form a saturated heterocyclic ring; and each R5, R6, R7 and R8 is independently selected from hydrogen, halogen, hydroxy; C1-C6 alkyl optionally substituted with hydroxy; alkylthio C1-C6; C1-C6 alkoxy optionally substituted with halogen; C1-C6 alkyl-carbonyl, C1-C6 alkoxy-carbonyl, and oxazol-2-yl; comprising converting a compound of formula (IV), or a salt thereof, wherein Q, R1, R2, R3, R4, R5, R6 and R7 are as defined above, to said compound of formula (I), or a salt thereof, in the presence of a catalyst, if necessary in an organic solvent; and, if desired, converting a compound of formula (I) to a salt thereof to another compound of formula (I); and/or, if desired, resolving an isomeric mixture of a compound of formula (I) in the individual isomers.

  一种制备式（I）化合物或其盐的方法，包括其异构混合物和单体异构体，其中Q = CR8-或= N-;每个R1、R2、R3和R4独立地选自氢、卤素、羟基、硝基、C1-C6烷基，可选地取代羟基；C1-C6烷基硫代基；C1-C6烷氧基，可选地取代卤素或C1-C6烷氧基；苯基-C1-C6烷基；苯基-C1-C6烷氧基；以及-N（RaRb）其中每个Ra和Rb独立地选自氢或C1-C6烷基，或Ra和Rb连同它们连接到的氮原子形成饱和杂环环；以及每个R5、R6、R7和R8独立地选自氢、卤素、羟基、C1-C6烷基，可选地取代羟基；C1-C6烷基硫代基；C1-C6烷氧基，可选地取代卤素；C1-C6烷基-羰基，C1-C6烷氧基-羰基和噁唑-2-基；包括在有机溶剂中在催化剂的存在下将式（IV）化合物或其盐转化为所述式（I）化合物或其盐，并且如果需要，将式（I）化合物转化为其盐以获得另一种式（I）化合物；如果需要，在单体异构体中分离式（I）化合物的异构混合物。
• Process for preparing 2-(2-pyridylmethyl)-sulfinyl-1H-benzimidazoles and the intermediate compounds used therein
  申请人：Palomo Nicolau Francisco Eugenio

  公开号：US20100210846A1

  公开（公告）日：2010-08-19

  The present invention relates to a process for preparing 2-(2-pyridylmethyl)sulphinyl-1H-benzimidazoles that are proton pump inhibitors, using as intermediates 2-benzimidazolyl-sulphinic acid derivatives. The present invention also relates to the intermediate compounds, their use and a process for the preparation thereof. These novel intermediate compounds are 2-benzimidazolylsulphinicacid esters that are obtained from their corresponding alkaline salts, which are in turn obtained by oxidation of substituted 2-mercaptobenzimidazoles. The intermediate compounds of the invention are converted into 2-(2-pyridylmethyl)sulphinyl-1H-benzimidazoles by reaction with substituted 2-methylpyridines.

  本发明涉及一种制备质子泵抑制剂2-(2-吡啶甲基)亚磺酰基-1H-苯并咪唑的方法，其中使用2-苯并咪唑基-亚磺酸衍生物作为中间体。本发明还涉及中间体化合物、其用途和制备方法。这些新型中间体化合物是2-苯并咪唑基-亚磺酸酯，通过其对应的碱性盐的氧化得到。本发明的中间体化合物通过与取代的2-甲基吡啶反应转化为2-(2-吡啶甲基)亚磺酰基-1H-苯并咪唑。