N-benzyl-2-bromothiazol-4-carboxamide | 1449218-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-2-bromothiazol-4-carboxamide
• 英文别名: N-benzyl-2-bromothiazole-4-carboxamide；N-benzyl-2-bromo-1,3-thiazole-4-carboxamide
• CAS: 1449218-23-8
• 化学式: C₁₁H₉BrN₂OS
• 分子量: 297.175
• InChiKey: OLRVWSKLVHMCOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  499.6±28.0 °C(Predicted)
• 密度：
  1.569±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨基嘧啶 、 N-benzyl-2-bromothiazol-4-carboxamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.0h， 以53%的产率得到N-苄基-2-(嘧啶-4-基氨基)噻唑-4-羧酰胺
  参考文献：
  名称：

  Concise Synthesis and X-Ray Crystal Structure of N-Benzyl-2-(pyrimidin-4′-ylamino)-thiazole-4-carboxamide (Thiazovivin), a Small-Molecule Tool for Stem Cell Research

  摘要：

  Stem cell research is one of the most promising fields of modern biomedical research and regenerative medicine. Limited availability and ethical concerns suggest the renouncement of embryonic stem cells (ESCs), thus raising the need for more efficient procedures for the generation of stem cells, ideally through reprogramming of mammalian cells. The small molecule N-benzyl-2-(pyrimidin-4-ylamino)-thiazole-4-carboxamide (thiazovivin) is known to improve the generation of human induced pluripotent stem cells (iPSCs) from human fibroblasts. We herein describe a highly efficient procedure for the synthesis of thiazovivin over just five steps, which should be suitable for a large-scale application, and the first x-ray crystal structure of the target compound. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.745567
• 作为产物：
  描述：

  2-溴-4-噻唑羧酸 、 苄胺 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 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以73%的产率得到N-benzyl-2-bromothiazol-4-carboxamide
  参考文献：
  名称：

  Concise Synthesis and X-Ray Crystal Structure of N-Benzyl-2-(pyrimidin-4′-ylamino)-thiazole-4-carboxamide (Thiazovivin), a Small-Molecule Tool for Stem Cell Research

  摘要：

  Stem cell research is one of the most promising fields of modern biomedical research and regenerative medicine. Limited availability and ethical concerns suggest the renouncement of embryonic stem cells (ESCs), thus raising the need for more efficient procedures for the generation of stem cells, ideally through reprogramming of mammalian cells. The small molecule N-benzyl-2-(pyrimidin-4-ylamino)-thiazole-4-carboxamide (thiazovivin) is known to improve the generation of human induced pluripotent stem cells (iPSCs) from human fibroblasts. We herein describe a highly efficient procedure for the synthesis of thiazovivin over just five steps, which should be suitable for a large-scale application, and the first x-ray crystal structure of the target compound. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.745567

文献信息

• STEM CELL CULTURES
  申请人：Xu Yue

  公开号：US20110294761A1

  公开（公告）日：2011-12-01

  The present invention relates compounds for stabilizing cells and methods of their use.

  本发明涉及用于细胞稳定化的化合物及其使用方法。
• Stem cell cultures
  申请人：The Scripps Research Institute

  公开号：US08044201B2

  公开（公告）日：2011-10-25

  The present invention relates compounds for stabilizing cells and methods of their use.

  本发明涉及用于细胞稳定化的化合物及其使用方法。
• US20140273214A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Concise Synthesis and X-Ray Crystal Structure of <i>N</i>-Benzyl-2-(pyrimidin-4′-ylamino)-thiazole-4-carboxamide (Thiazovivin), a Small-Molecule Tool for Stem Cell Research
  作者：Oliver Ries、Markus Granitzka、Dietmar Stalke、Christian Ducho

  DOI：10.1080/00397911.2012.745567

  日期：2013.11.2

  Stem cell research is one of the most promising fields of modern biomedical research and regenerative medicine. Limited availability and ethical concerns suggest the renouncement of embryonic stem cells (ESCs), thus raising the need for more efficient procedures for the generation of stem cells, ideally through reprogramming of mammalian cells. The small molecule N-benzyl-2-(pyrimidin-4-ylamino)-thiazole-4-carboxamide (thiazovivin) is known to improve the generation of human induced pluripotent stem cells (iPSCs) from human fibroblasts. We herein describe a highly efficient procedure for the synthesis of thiazovivin over just five steps, which should be suitable for a large-scale application, and the first x-ray crystal structure of the target compound. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]