2-(4-fluoro-benzyl)-4-(4-fluoro-phenyl)-5,6,8,9-tetrahydro-pyrimido[4,5-d]azepine-7-carboxylic acid tert-butyl ester | 924654-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(4-fluoro-benzyl)-4-(4-fluoro-phenyl)-5,6,8,9-tetrahydro-pyrimido[4,5-d]azepine-7-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepine-7-carboxylate
• CAS: 924654-68-2
• 化学式: C₂₆H₂₇F₂N₃O₂
• 分子量: 451.516
• InChiKey: DEBCZTRGKYYNFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-fluoro-benzyl)-4-(4-fluoro-phenyl)-5,6,8,9-tetrahydro-pyrimido[4,5-d]azepine-7-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-Fluoro-benzyl)-4-(4-fluoro-phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine
  参考文献：
  名称：

  2-Alkyl-4-aryl-pyrimidine fused heterocycles as selective 5-HT2A antagonists

  摘要：

  The synthesis and SAR for a novel series of 2-alkyl-4-aryl-tetrahydro-pyrido-pyrimidines and 2-alkyl-4-aryl-tetrahydropyrimido-azepines is described. Representative compounds were shown to be subtype selective 5-HT2A antagonists. Optimal placement of a basic nitrogen relative to the pyrimidine and the presence of a 4-fluorophenyl group in the pyrimidine 4-position was found to have a profound effect on affinity and selectivity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.090
• 作为产物：
  描述：

  tert-butyl 2-(4-fluorobenzyl)-4-[(trifluoromethylsulfonyl)oxy]-5,6,8,9-tetrahydropyrimido[4,5-d]azepine-7-carboxylate 、 4-氟苯硼酸 在 Pd(dppf)Cl*CH₂Cl₂ 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(4-fluoro-benzyl)-4-(4-fluoro-phenyl)-5,6,8,9-tetrahydro-pyrimido[4,5-d]azepine-7-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  2-Alkyl-4-aryl-pyrimidine fused heterocycles as selective 5-HT2A antagonists

  摘要：

  The synthesis and SAR for a novel series of 2-alkyl-4-aryl-tetrahydro-pyrido-pyrimidines and 2-alkyl-4-aryl-tetrahydropyrimido-azepines is described. Representative compounds were shown to be subtype selective 5-HT2A antagonists. Optimal placement of a basic nitrogen relative to the pyrimidine and the presence of a 4-fluorophenyl group in the pyrimidine 4-position was found to have a profound effect on affinity and selectivity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.090

文献信息

• PYRIMIDINE COMPOUNDS AS SEROTONIN RECEPTOR MODULATORS
  申请人：Dvorak A. Curt

  公开号：US20070032481A1

  公开（公告）日：2007-02-08

  Certain pyrimidine-containing compounds are serotonin receptor modulators useful in the treatment of serotonin-mediated diseases.

  某些含嘧啶的化合物是有效的血清素受体调节剂，可用于治疗血清素介导的疾病。
• Pyrimidine compounds as serotonin receptor modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US07598255B2

  公开（公告）日：2009-10-06

  Certain pyrimidine-containing compounds are serotonin receptor modulators useful in the treatment of serotonin-mediated diseases.

  某些含嘧啶的化合物是血清素受体调节剂，可用于治疗与血清素相关的疾病。
• US7598255B2
  申请人：——

  公开号：US7598255B2

  公开（公告）日：2009-10-06
• US8618288B2
  申请人：——

  公开号：US8618288B2

  公开（公告）日：2013-12-31
• 2-Alkyl-4-aryl-pyrimidine fused heterocycles as selective 5-HT2A antagonists
  作者：Brock T. Shireman、Curt A. Dvorak、Dale A. Rudolph、Pascal Bonaventure、Diane Nepomuceno、Lisa Dvorak、Kirsten L. Miller、Timothy W. Lovenberg、Nicholas I. Carruthers

  DOI：10.1016/j.bmcl.2008.01.090

  日期：2008.3

  The synthesis and SAR for a novel series of 2-alkyl-4-aryl-tetrahydro-pyrido-pyrimidines and 2-alkyl-4-aryl-tetrahydropyrimido-azepines is described. Representative compounds were shown to be subtype selective 5-HT2A antagonists. Optimal placement of a basic nitrogen relative to the pyrimidine and the presence of a 4-fluorophenyl group in the pyrimidine 4-position was found to have a profound effect on affinity and selectivity. (c) 2008 Elsevier Ltd. All rights reserved.