N-((S)-2-(3-fluorophenyl)-1-((2S,4R)-tetrahydro-4-(3-hydroxy-3-methylbutyl)-5-oxofuran-2-yl)ethyl)quinoxaline-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-((S)-2-(3-fluorophenyl)-1-((2S,4R)-tetrahydro-4-(3-hydroxy-3-methylbutyl)-5-oxofuran-2-yl)ethyl)quinoxaline-2-carboxamide
• 英文别名: quinoxaline-2-carboxylic acid {2-(3-fluorophenyl)-1-[4-(3-hydroxy-3-methyl-butyl)-5-oxo-tetrahydro-furan-2-yl]-ethyl}-amide；N-[(1S)-2-(3-fluorophenyl)-1-[(2S,4R)-4-(3-hydroxy-3-methylbutyl)-5-oxooxolan-2-yl]ethyl]quinoxaline-2-carboxamide
• 化学式: C₂₆H₂₈FN₃O₄
• 分子量: 465.524
• InChiKey: KIEIHOHFYMCOJL-FHZYATBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((S)-2-(3-fluorophenyl)-1-((2S,4R)-tetrahydro-4-(3-hydroxy-3-methylbutyl)-5-oxofuran-2-yl)ethyl)quinoxaline-2-carboxamide 在 氨 作用下， 以 甲醇 为溶剂， 生成 CP 481715
  参考文献：
  名称：

  [EN] CRYSTAL FORMS OF QUINOXALINE-2-CARBOXYLIC ACID [4-CARBAMOYL-1-(3-FLUOROBENZYL)-2,7-DIHYDROXY-7-METHYL-OCTYL]-AMIDE
  [FR] FORMES CRISTALLINES D'ACIDE QUINOXALINE-2-CARBOXYLIQUE [4-CARBAMOYL-1-(3-FLUOROBENZYL)-2,7-DIHYDROXY-7-METHYL-OCTYL]-AMIDE

  摘要：

  该发明涉及喹喔啉-2-羧酸[4-氨基甲酰基-1-(3-氟苯基)-2,7-二羟基-7-甲基辛基]-酰胺的晶型，用于通过拮抗CCR1受体来治疗或预防某种疾病或状况，以及其制备和使用方法。

  公开号：

  WO2004014875A1
• 作为产物：
  描述：

  tert-butyl (S)-2-(3-fluorophenyl)-1-((2S,4R)-tetrahydro-4-(3-methylbut-2-enyl)-5-oxofuran-2-yl)ethylcarbamate 在 磷酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 10.0h， 生成 N-((S)-2-(3-fluorophenyl)-1-((2S,4R)-tetrahydro-4-(3-hydroxy-3-methylbutyl)-5-oxofuran-2-yl)ethyl)quinoxaline-2-carboxamide
  参考文献：
  名称：

  Process Development of CP-481715, a Novel CCR1 Antagonist

  摘要：

  Process development for the synthesis of 2-quinoxalinecarboxamide, N-[(1S,2S,4R)-4-(aminocarbonyl)-1-[(3-fluorophenyl)methyl]-2,7-dihydroxy-7-methyloctyl] is described. An optimized,and streamlined process starting from lactone 2 was developed: Lactone 2 was alkylated diastereoselectively with prenyl bromide, followed by deprotection of the N-Boc group and concomitant hydration of the olefin. Aminolysis of the lactone in methanolic ammonia afforded the titled compound.

  DOI：

  10.1021/op050059w

文献信息

• [EN] CRYSTAL FORMS OF QUINOXALINE-2-CARBOXYLIC ACID [4-CARBAMOYL-1-(3-FLUOROBENZYL)-2,7-DIHYDROXY-7-METHYL-OCTYL]-AMIDE<br/>[FR] FORMES CRISTALLINES D'ACIDE QUINOXALINE-2-CARBOXYLIQUE [4-CARBAMOYL-1-(3-FLUOROBENZYL)-2,7-DIHYDROXY-7-METHYL-OCTYL]-AMIDE
  申请人：PFIZER PROD INC

  公开号：WO2004014875A1

  公开（公告）日：2004-02-19

  The invention relates to crystal forms of quinoxaline-2-carboxylic acid [4-carbamoyl-1-(3-fluorobenzyl)-2,7-dihydroxy-7-methyl-octyl]-amide, useful in treating or preventing a disorder or condition by antogonizing the CCR1 receptor, and to their methods of preparation and use.

  该发明涉及喹喔啉-2-羧酸[4-氨基甲酰基-1-(3-氟苯基)-2,7-二羟基-7-甲基辛基]-酰胺的晶型，用于通过拮抗CCR1受体来治疗或预防某种疾病或状况，以及其制备和使用方法。
• Org. Process Res. Dev. 2005, 9, 466-471
  作者：

  DOI：——

  日期：——
• Process Development of CP-481715, a Novel CCR1 Antagonist
  作者：Bryan Li、Brian Andresen、Matthew F. Brown、Richard A. Buzon、Charles K.-F. Chiu、Michel Couturier、Eric Dias、Frank J. Urban、V. John Jasys、John C. Kath、William Kissel、Tung Le、Z. Jane Li、Joanna Negri、Christopher S. Poss、John Tucker、David Whritenour、Kathleen Zandi

  DOI：10.1021/op050059w

  日期：2005.7.1

  Process development for the synthesis of 2-quinoxalinecarboxamide, N-[(1S,2S,4R)-4-(aminocarbonyl)-1-[(3-fluorophenyl)methyl]-2,7-dihydroxy-7-methyloctyl] is described. An optimized,and streamlined process starting from lactone 2 was developed: Lactone 2 was alkylated diastereoselectively with prenyl bromide, followed by deprotection of the N-Boc group and concomitant hydration of the olefin. Aminolysis of the lactone in methanolic ammonia afforded the titled compound.