Ethyl 6-[4-(5-bromopentanoylamino)phenyl]-1-(4-methoxycyclohexa-1,3-dien-1-yl)-7-oxo-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 6-[4-(5-bromopentanoylamino)phenyl]-1-(4-methoxycyclohexa-1,3-dien-1-yl)-7-oxo-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxylate
• 英文别名: ethyl 6-[4-(5-bromopentanoylamino)phenyl]-1-(4-methoxycyclohexa-1,3-dien-1-yl)-7-oxo-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxylate
• 化学式: C₂₇H₃₁BrN₄O₅
• 分子量: 571.5
• InChiKey: UGCURFHNNPBDCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

文献信息

• [EN] A METHOD OF PREPARING APIXABAN<br/>[FR] PROCÉDÉ DE PRÉPARATION D'APIXABAN
  申请人：ZENTIVA KS

  公开号：WO2014075648A1

  公开（公告）日：2014-05-22

  The object of the present solution provides a method preparing apixaban of formula (I) in which ethyl 6-(4-iodophenyl)- 1 -(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4- c]pyridine-3-carboxylate of formula (III) is reacted with piperidin-2-one of formula (IV) in the presence of a base and a ligand and under catalysis by copper or by copper (II) ions, wherein a phosphoric acid salt is used as the base and an amine from the group of 1,2-diamines is used as the ligand in an aprotic solvent, and ethyl 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1- piperidin-1-yl)phenyl] -4, 5,6,7-tetrahydro-1H-pyrazol-[3,4-c]pyridine-3-carbvoxylate is prepared, which is converted, by reaction with ammonia in a suitable solvent, to apixaban of formula (I), which is isolated and optionally crystallized.

  本解决方案的目的是提供一种制备化合物apixaban的方法，其中以式(I)的乙酸6-(4-碘苯基)-1-(4-甲氧基苯基)-7-氧代-4,5,6,7-四氢-1H-吡唑并[3,4-c]吡啶-3-羧酸乙酯的式(III)与式(IV)的哌啶-2-酮在碱和配体的存在下，通过铜或铜(II)离子的催化反应，其中磷酸盐被用作碱，1,2-二胺类化合物被用作配体，在无极性溶剂中制备了乙酸1-(4-甲氧基苯基)-7-氧代-6-[4-(2-氧代-1-哌啶-1-基)苯基]-4,5,6,7-四氢-1H-吡唑并[3,4-c]吡啶-3-羧基乙酸酯，通过与适当溶剂中的氨反应，将其转化为式(I)的apixaban，然后对其进行分离和可选择结晶。