(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanamide | 1103518-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanamide
• 英文别名: (I+/-S)-5-Fluoro-I+/--methyl-1H-indole-3-propanamide
• CAS: 1103518-33-7
• 化学式: C₁₂H₁₃FN₂O
• 分子量: 220.246
• InChiKey: OQFBMAIYBFICEO-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropan-1-amine
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085
• 作为产物：
  描述：

  (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 氨 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以87%的产率得到(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanamide
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085

文献信息

• PCSK9 antagonists bicyclo-compounds
  申请人：Merck Sharp & Dohme Corp.

  公开号：US11306125B2

  公开（公告）日：2022-04-19

  Disclosed are compounds of Formula I, or a salt thereof cyclic polypeptide of Formula I: Formula I where A, B, E, R4, and R8 are as defined herein, which compounds have properties for antagonizing PCSK9. Also described are pharmaceutical formulations comprising the compounds of Formula I or their salts, and methods of treating cardiovascular disease and conditions related to PCSK9 activity, e.g. atherosclerosis, hypercholesterolemia, coronary heart disease, metabolic syndrome, acute coronary syndrome, or related cardiovascular disease and cardiometabolic conditions

  公开了式 I 的化合物或其盐式 I 的环状多肽：式 I 其中 A、B、E、R4 和 R8 如本文所定义，这些化合物具有拮抗 PCSK9 的特性。还描述了包含式 I 化合物或其盐的药物制剂，以及治疗心血管疾病和与 PCSK9 活性有关的病症（如动脉粥样硬化、高胆固醇血症、冠心病、代谢综合征、急性冠状动脉综合征或相关心血管疾病和心脏代谢病症）的方法。
• PCSK9 ANTAGONISTS BICYCLO-COMPOUNDS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20210214395A1

  公开（公告）日：2021-07-15

  Disclosed are compounds of Formula I, or a salt thereof cyclic polypeptide of Formula I: Formula I where A, B, E, R 4 , and R 8 are as defined herein, which compounds have properties for antagonizing PCSK9. Also described are pharmaceutical formulations comprising the compounds of Formula I or their salts, and methods of treating cardiovascular disease and conditions related to PCSK9 activity, e.g. atherosclerosis, hypercholesterolemia, coronary heart disease, metabolic syndrome, acute coronary syndrome, or related cardiovascular disease and cardiometabolic conditions
• First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist
  作者：Antonia Nikitenko、Asaf Alimardanov、Jay Afragola、Jean Schmid、Livia Kristofova、Deborah Evrard、Nicole T. Hatzenbuhler、Vasilios Marathias、Gary Stack、Steve Lenicek、John Potoski

  DOI：10.1021/op8002085

  日期：2009.1.16

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.