tert-butyl [6-bromo-3-(cyclobutylamino)-2-oxopyrazin-1(2H)-yl]acetate | 374671-03-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl [6-bromo-3-(cyclobutylamino)-2-oxopyrazin-1(2H)-yl]acetate
• 英文别名: 6-Bromo-1-t-butoxycarbonylmethyl-3-(N-cyclobutylamino)pyrazinone；tert-butyl 2-[6-bromo-3-(cyclobutylamino)-2-oxopyrazin-1-yl]acetate
• CAS: 374671-03-1
• 化学式: C₁₄H₂₀BrN₃O₃
• 分子量: 358.235
• InChiKey: OAKLPCTVMYIUPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl [6-bromo-3-(cyclobutylamino)-2-oxopyrazin-1(2H)-yl]acetate 、 benzyl pent-4-ynoate 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以47%的产率得到benzyl 5-[1-(2-tert-butoxy-2-oxoethyl)-5-(cyclobutylamino)-6-oxo-1,6-dihydropyrazin-2-yl]pent-4-ynoate
  参考文献：
  名称：

  Synthesis of a versatile 2 (1H)-pyrazinone core for the preparation of Tissue Factor-Factor VIIa inhibitors

  摘要：

  A new, general synthetic route to 2(1H)-pyrazinones 11 is described The four-step synthesis is accomplished utilizing a regioselective hydrolysis and N-alkylation These compounds efficiently undergo metal-catalyzed cross-coupling reactions to install P2 diversity groups in the 6-position, which can be used to refine the SAR of the S2 pocket of the Tissue Factor/Factor VIIa (TF/VIIa) complex (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.026
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 6-bromo-3-(cyclobutylamino)pyrazin-2-ol 在 calcium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以87%的产率得到tert-butyl [6-bromo-3-(cyclobutylamino)-2-oxopyrazin-1(2H)-yl]acetate
  参考文献：
  名称：

  Synthesis of a versatile 2 (1H)-pyrazinone core for the preparation of Tissue Factor-Factor VIIa inhibitors

  摘要：

  A new, general synthetic route to 2(1H)-pyrazinones 11 is described The four-step synthesis is accomplished utilizing a regioselective hydrolysis and N-alkylation These compounds efficiently undergo metal-catalyzed cross-coupling reactions to install P2 diversity groups in the 6-position, which can be used to refine the SAR of the S2 pocket of the Tissue Factor/Factor VIIa (TF/VIIa) complex (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.026

文献信息

• Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
  申请人：Pharmacia Corporation

  公开号：US20040006230A1

  公开（公告）日：2004-01-08

  The invention relates to substituted polycyclic aryl and heteroaryl pyrazinone compounds useful as inhibitors of serine proteases of the coagulation cascade and compounds, compositions and methods for anticoagulant therapy for the treatment and prevention of a variety of thrombotic conditions including coronary artery and cerebrovascular diseases.

  该发明涉及替代多环芳基和杂环芳基吡唑酮化合物，其可用作凝血级联中丝氨酸蛋白酶的抑制剂，并提供了用于治疗和预防包括冠状动脉和脑血管疾病在内的各种血栓性疾病的化合物、组合物和抗凝治疗方法。
• Substituted polycyclic aryl and heteroarpyl pyrazinones useful for selective inhibition of the coagulation cascade
  申请人：Warner-Lambert Company

  公开号：US07119094B1

  公开（公告）日：2006-10-10

  The invention relates to substituted polycyclic aryl and heteroaryl pyrazinone compounds useful as inhibitors of serine proteases of the coagulation cascade and compounds, compositions and methods for anticoagulant therapy for the treatment and prevention of a variety of thrombotic conditions including coronary artery and cerebrovascular diseases.

  本发明涉及取代的多环芳基和杂环芳基吡唑酮化合物，其可用作凝血级联中丝氨酸蛋白酶的抑制剂，以及用于治疗和预防包括冠状动脉和脑血管疾病在内的各种血栓症状的化合物、组合物和抗凝治疗方法。
• US6908919B2
  申请人：——

  公开号：US6908919B2

  公开（公告）日：2005-06-21
• US7119094B1
  申请人：——

  公开号：US7119094B1

  公开（公告）日：2006-10-10
• Synthesis of a versatile 2 (1H)-pyrazinone core for the preparation of Tissue Factor-Factor VIIa inhibitors
  作者：Darin E. Jones、Michael S. South

  DOI：10.1016/j.tet.2010.02.026

  日期：2010.4

  A new, general synthetic route to 2(1H)-pyrazinones 11 is described The four-step synthesis is accomplished utilizing a regioselective hydrolysis and N-alkylation These compounds efficiently undergo metal-catalyzed cross-coupling reactions to install P2 diversity groups in the 6-position, which can be used to refine the SAR of the S2 pocket of the Tissue Factor/Factor VIIa (TF/VIIa) complex (C) 2010 Elsevier Ltd All rights reserved