Methyl-{(S)-1-[methyl-((R)-1-methyl-pyrrolidin-3-yl)-carbamoyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester | 762283-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: Methyl-{(S)-1-[methyl-((R)-1-methyl-pyrrolidin-3-yl)-carbamoyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester
• CAS: 762283-12-5
• 化学式: C₁₇H₃₂N₄O₃
• 分子量: 340.466
• InChiKey: VENOTNMXOMYUAJ-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  56.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl-{(S)-1-[methyl-((R)-1-methyl-pyrrolidin-3-yl)-carbamoyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester 在 TEA 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 (3S)-3-[(5-bromothiophene-2-carbonyl)-methylamino]-N-methyl-N-[(3R)-1-methylpyrrolidin-3-yl]pyrrolidine-1-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of biarylcarboxamide bis-aminopyrrolidine urea derived small-molecule antagonists of the melanin-concentrating hormone receptor-1 (MCH-R1)

  摘要：

  A novel series of bis-aminopyrrolidine ureas containing either a 4-biphenylcarboxmide or 5-phenyl-2-thiophenecarboxamide group have been identified as potent and functional antagonists of the melanin-concentrating hormone receptor-1. Syntheses and SAR are described, which led to the discovery of compounds with high binding affinity (K-i = 1 nM) for the receptor. Preliminary in vitro metabolic stability data are also reported for key compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.015
• 作为产物：
  描述：

  ((R)-1-benzylpyrrolidin-3-yl)-methyl-carbamic acid 4-nitrophenyl ester 在 palladium on activated charcoal ammonium formate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl-{(S)-1-[methyl-((R)-1-methyl-pyrrolidin-3-yl)-carbamoyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Bis(aminopyrrolidine)-derived ureas (APUs) as potent MCH1 receptor antagonists

  摘要：

  Ureas derived from two substituted 3-aminopyrrolidine subunits were prepared as constrained analogs of a linear lead compound and tested as antagonists of the MCH1 receptor. The series was optimized for substitution and stereochemistry to generate a functional antagonist with a K-i of 3.3 nM and IC50 of 12 nM (GTPgammaS). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.036