N-(2-氨基-4,5,6,7-四氢苯并噻唑-6-基)-丙酰胺 | 375824-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-(2-氨基-4,5,6,7-四氢苯并噻唑-6-基)-丙酰胺
• 英文名称: 2-amino-6-(propionylamino)-4,5,6,7-tetrahydrobenzothiazole
• 英文别名: 2-amino-6-propionamido-4,5,6,7-tetrahydrobenzothiazole；(+/-)-2-amino-6-propanamido-4,5,6,7-tetrahydrobenzthiazole；(R,S)-2-amino-6-propionylamino-4,5,6,7-tetrahydrobenzothiazole；(+/-)-2-amino-6-propanamido-4,5,6,7-tetrahydrobenzothiazole；N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)propionamide；N-(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)propanamide
• CAS: 375824-96-7
• 化学式: C₁₀H₁₅N₃OS
• mdl: MFCD03839823
• 分子量: 225.315
• InChiKey: VVPFOYOFGUBZRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  N-(2-氨基-4,5,6,7-四氢苯并噻唑-6-基)-丙酰胺 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以91%的产率得到(±)-普拉克索
  参考文献：
  名称：

  一种盐酸普拉克索的制备方法

  摘要：

  本发明公开了一种盐酸普拉克索的制备方法，包括以下步骤：对氨基环己醇经丙酰氯缩合保护氨基得到对丙酰基环己醇，然后经催化氧化得到对丙酰基环己酮，再经氧化溴化和Hantzsch缩合得到2‑氨基‑6‑丙酰氨基‑4，5，6，7‑四氢苯并噻唑，再经二异丁基氢化铝还原得到2‑氨基‑6‑丙氨基‑4，5，6，7‑四氢苯并噻唑，最后经L‑(+)‑酒石酸拆分和成盐得盐酸普拉克索。本发明提出的一种盐酸普拉克索的制备方法，原料廉价易得，操作方便简单，路线新颖、绿色环保，收率高，制备得到的盐酸普拉克索纯度好。

  公开号：

  CN109232471B
• 作为产物：
  描述：

  2-amino-6-propionylamino-4,5,6,7-tetrahydrobenzothiazole hydrobromide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 N-(2-氨基-4,5,6,7-四氢苯并噻唑-6-基)-丙酰胺
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF PRAMIPEXOLE AND NEW ANHYDROUS FORMS OF ITS DIHYDROCHLORIDE

  摘要：

  本发明提供了制备(−)普拉米贝克索或其盐酸酸加成物的I式的过程。本发明还提供了无水普拉米贝克索二盐酸盐的新型多晶型A和B。

  公开号：

  US20090062549A1

文献信息

• [EN] PROCESS FOR PREPARING CHIRALLY PURE 2-AMINO-6-(ALKYL)AMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLES BY LIQUID CHROMATOGRAPHIC RESOLUTION<br/>[FR] PROCESSUS POUR PRÉPARER DES 2-AMINO-6-(ALKYL)AMINO-4,5,6,7-TÉTRAHYDROBENZOTHIAZOLES CHIRALEMENT PURS PAR RÉSOLUTION CHROMATOGRAPHIQUE EN PHASE LIQUIDE
  申请人：AMR TECHNOLOGY INC

  公开号：WO2006012276A1

  公开（公告）日：2006-02-02

  Processes for obtaining single enantiomers of 2-amino-6-(alkyl)amino­4,5,6,7-tetrahydrobenzothiazoles by liquid chromatography are disclosed.

  通过液相色谱法获得2-氨基-6-(烷基)氨基-4,5,6,7-四氢苯并噻唑的单对映体的过程被披露。
• Process for the reduction of (S)-2-amino-6-propionamido-4,5,6,7-tetrahydrobenzo-thiazole
  申请人：Gribun Irina

  公开号：US20060069263A1

  公开（公告）日：2006-03-30

  A process is disclosed for the reduction of (S)-2-amino-6-propionamido-4,5,6,7-tetrahydrobenzothiazole, which comprises reacting (S)-2-amino-6-propionamido-4,5,6,7-tetrahydrobenzothiazole with a borane reagent in the presence of suitable organic solvent to yield (S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole base, which may be converted to an acid addition salt thereof. The process provided herein can be easily, conveniently and inexpensively scaled-up.

  本公开了一种还原(S)-2-氨基-6-丙酰胺基-4,5,6,7-四氢苯并噻唑醇的方法，包括在适当的有机溶剂存在下，将(S)-2-氨基-6-丙酰胺基-4,5,6,7-四氢苯并噻唑醇与硼烷试剂反应，得到(S)-2-氨基-6-丙基氨基-4,5,6,7-四氢苯并噻唑醇碱，可转化为其酸盐。本文提供的方法可以轻松、方便、廉价地进行扩大规模。
• Novel process for preparing pramipexole and its optical isomeric mixture by reduction with sodium triacetoxyborohydride
  申请人：Xia Guangxin

  公开号：US20060148866A1

  公开（公告）日：2006-07-06

  A novel process is provided for producing pramipexole base or its optical isomeric mixture as defined hereinabove i.e. (R,S)-2-amino-6-propyl-4,5,6,7-tetrahydrobenzothiazole avoiding the use of borane tetrahydrofuran complex and using a more convenient reducing agent like sodium triacetoxyborohydride instead. The provided process comprises reacting the starting material (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole or its optical isomeric mixture as defined hereinabove i.e. (R,S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole with propionaldehyde in an organic solvent to obtain the respective enamine, which is subsequently reduced in situ, optionally without isolation, to obtain pramipexole or its optical isomeric mixture as defined hereinabove i.e. (R,S)-2-amino-6-propyl-4,5,6,7-tetrahydrobenzothiazole, and the acid addition salts thereof. The present invention also provides a process for purifying pramipexole dihydrochloride or the dihydrochloride salt of its optical isomeric mixture as defined hereinabove i.e. (R,S)-2-amino-6-propyl-4,5,6,7-tetrahydrobenzothiazole dihydrochloride by re-crystallization from a suitable solvent.

  本发明提供了一种生产普拉米贝克索尔碱或其光学异构体混合物的新工艺，即避免使用四氢呋喃硼烷复合物，而使用更方便的还原剂如三乙酰氧基硼氢化钠。所提供的工艺包括将起始物质(S)-2,6-二氨基-4,5,6,7-四氢苯并噻唑或其光学异构体混合物如上所述，即(R,S)-2,6-二氨基-4,5,6,7-四氢苯并噻唑与丙醛在有机溶剂中反应，得到相应的烯胺，然后原位还原，可选地不进行分离，得到普拉米贝克索尔或其光学异构体混合物如上所述，即(R,S)-2-氨基-6-丙基-4,5,6,7-四氢苯并噻唑及其酸盐。本发明还提供了一种从适当溶剂中重新结晶纯化普拉米贝克索尔二盐酸盐或其光学异构体混合物如上所述，即(R,S)-2-氨基-6-丙基-4,5,6,7-四氢苯并噻唑二盐酸盐的工艺。
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DU MONOHYDRATE DU DICHLORHYDRATE DE PRAMIPEXOLE
  申请人：PIRAMAL ENTPR LTD

  公开号：WO2015155704A1

  公开（公告）日：2015-10-15

  The present invention relates to an improved process for the preparation of the dihydrochloride monohydrate salt of (S)-2-amino-4,5,6,7-tetrahydro-6- (propylamino)benzothiazole (the compound of formula I) comprising reacting the compound of formula II with n-propanal and sodium borohydride using a mixture of methanol and dichloromethane (DCM) as the solvent to obtain the compound of formula I; followed by converting the compound of formula I into its monohydrochloride salt; purifying the monohydrochloride salt of the compound of formula I; and finally converting the pure monohydrochloride salt of the compound of formula I into the dihydrochloride monohydrate salt.

  本发明涉及一种改进的制备(S)-2-氨基-4,5,6,7-四氢-6-(丙基氨基)苯并噻唑的二盐酸盐一水合物（化合物I）的过程，包括将化合物II与正丙醛和硼氢化钠在甲醇和二氯甲烷（DCM）的混合溶剂中反应以获得化合物I；然后将化合物I转化为其单盐酸盐；纯化化合物I的单盐酸盐；最后将纯净的化合物I的单盐酸盐转化为二盐酸盐一水合物。
• Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole and compounds therefor
  申请人：——

  公开号：US20020103240A1

  公开（公告）日：2002-08-01

  A process for resolving or enriching (R,S) 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole (pramipexole) into optical isomers uses a monovalent salt thereof, e.g. pramipexole monohydrochloride, as a substrate. The monovalent salt is treated with an optically active acid, e.g. with L(+)-tartaric acid, to yield a diastereomeric mixed salt. The mixed salt is subjected to fractional crystallization to yield an optically enriched mixed salt. The mixed salt can be treated with base to liberate the desired isomer of pramipexole.

  将(R,S)-2-氨基-6-丙基氨基-4,5,6,7-四氢苯并噻唑醇（普拉米贝克索）分离或富集成光学异构体的过程使用其一价盐，例如普拉米贝克索单盐酸盐，作为底物。将这一价盐与光学活性酸处理，例如与L(+)-酒石酸处理，得到一个对映异构的混合盐。将混合盐经过分级结晶处理，得到光学富集的混合盐。混合盐可以用碱处理以释放普拉米贝克索的所需异构体。