(R/S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl methanesulfonate | 1433546-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡嗪类
• 英文名称: (R/S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl methanesulfonate
• 英文别名: [4-oxo-4-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl] methanesulfonate
• CAS: 1433546-53-2
• 化学式: C₁₇H₁₆F₆N₄O₄S
• 分子量: 486.395
• InChiKey: JTCFOVFAUXUUJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (R/S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl methanesulfonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 27.0h， 生成 (R/S)-3-azido-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
  参考文献：
  名称：

  [EN] PROCESSES FOR PREPARING 4-OXO-4-[3-(TRIFLUOROMETHYL)-5,6- DIHYDRO [L,2,41-TRIAZOLO[43-A]PYRAZIN-7(8H)-YL]-L-(2,4,5- TRIFLUOROPHENYL)BUTAN-2-AMINE
  [FR] PROCÉDÉS DE PRÉPARATION DE 4-OXO-4-[3-(TRIFLUOROMÉTHYL)-5,6-DIHYDRO- [L,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]-1-(2,4,5-TRIFLUOROPHÉNYL)- BUTAN-2-AMINE

  摘要：

  本发明涉及通过新颖的方法合成式(I)的4-氧代-4-[3-(三氟甲基)-5,6-二氢[1,2,4]-三唑并[4,3-a]吡嗪-7(8H)-基]-1-(2,4,5-三氟苯基)丁-2-胺，其可以是其消旋（R/S）形式或其任何光学活性（S）或（R）形式或任何形式的对映过量混合物。该发明还涉及在制备式(I)化合物中有用的某些新型中间体及其制备方法。

  公开号：

  WO2013065066A1

文献信息

• PROCESS FOR PREPARING AN INTERMEDIATE OF SITAGLIPTIN VIA ENZYMATIC CONVERSION
  申请人：Mendirata Sanjeev Kumar

  公开号：US20130289276A1

  公开（公告）日：2013-10-31

  The invention provides a process for preparing 3-hydroxy-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one (Formula I), into its racemic (R/S) form or any of its optically active (S) or (R) forms or enantiomeric excess mixture of any of the forms comprising: a) reacting 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one of formula (III) with a suitable oxidoreductase enzymes or its suitable variants in the presence of suitable conditions and co-factor; and b) isolating 3-hydroxy-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one, into its racemic (R/S) form or any of its optically active (S) or (R) forms or enantiomeric excess mixture of any of the forms.

  该发明提供了一种制备3-羟基-1-(3-(三氟甲基)-5,6-二氢-[1,2,4]三唑并[4,3-a]吡嗪-7(8H)-基)-4-(2,4,5-三氟苯基)丁酮（化学式I）的过程，制备其拉氏（R/S）形式或其任何光学活性（S）或（R）形式或任何形式的对映体过量混合物，包括：a) 在适当条件和辅因子的存在下，将化学式（III）的4-氧代-4-[3-(三氟甲基)-5,6-二氢-[1,2,4]三唑并[4,3-a]吡嗪-7(8H)-基]-1-(2,4,5-三氟苯基)丁酮与适当的氧化还原酶酶或其适当变体反应；和b) 分离3-羟基-1-(3-(三氟甲基)-5,6-二氢-[1,2,4]三唑并[4,3-a]吡嗪-7(8H)-基)-4-(2,4,5-三氟苯基)丁酮，制备其拉氏（R/S）形式或其任何光学活性（S）或（R）形式或任何形式的对映体过量混合物。
• [EN] PROCESS FOR PREPARING AN INTERMEDIATE OF SITAGLIPTIN VIA ENZYMATIC CONVERSION<br/>[FR] MÉTHODE DE PRÉPARATION D'UN INTERMÉDIAIRE DE SITAGLIPTINE PAR CONVERSION ENZYMATIQUE
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2012046254A2

  公开（公告）日：2012-04-12

  The invention provides a process for preparing 3 -hydroxy- 1 -(3- (trifluoromethyl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5- trifluorophenyl) butan-l-one (Formula I), into its racemic (R/S) form or any of its optically active (S) or (R) forms or enantiomeric excess mixture of any of the forms comprising: a) reacting 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[l,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-l- (2,4,5-trifluorophenyl)butan-2-one of formula (III) with a suitable oxidoreductase enzymes or its suitable variants in the presence of suitable conditions and co-factor b) isolating 3-hydroxy-l-(3-(trifluoromethyl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl)-4-(2,,4,5-trifluorophenyl) butan-l-one, into its racemic (R/S) form or any of its optically active (S) or (R) forms or enantiomeric excess mixture of any of the forms