5-(2-aminoethyl)-1-(4-methoxyphenyl)-1H-pyrazole-4-{N-[2-(ethoxycarbonyl)ethyl]carboxamide} hydrochloride | 1188338-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-aminoethyl)-1-(4-methoxyphenyl)-1H-pyrazole-4-{N-[2-(ethoxycarbonyl)ethyl]carboxamide} hydrochloride
• CAS: 1188338-85-3
• 化学式: C₁₈H₂₄N₄O₄*ClH
• 分子量: 396.874
• InChiKey: XYTZSOCZRVCWOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  108.47
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2,3,4,5,6-pentafluorophenyl) 2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetate 、 5-(2-aminoethyl)-1-(4-methoxyphenyl)-1H-pyrazole-4-{N-[2-(ethoxycarbonyl)ethyl]carboxamide} hydrochloride 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以129 mg的产率得到5-(3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-yl)-1-(4-methoxyphenyl)-1H-pyrazole-4-{N-[2-(ethoxycarbonyl)ethyl]carboxamide}
  参考文献：
  名称：

  A synthesis of 1-substituted 5-[2-(acylamino)ethyl]-1H-pyrazole-4-carboxamides

  摘要：

  A seven-step synthesis of 1-substituted 5-(2-acylaminoethyl)-1H-pyi-azole-4-carboxamides 20 as the pyrazole analogues of histamine was developed. The synthesis starts with a three-step preparation of N(1)-substituted methyl 5-(2-tert-butoxycarbonylaminoethyl)-1H-pyrazole-4-carboxylates 7 from commercially available Boc-beta-alanine (1). Subsequent four-step transformation of the key-intermediates 7 into the final products 20 was performed following two complementary reaction sequences comprising acidolytic removal of the Boc group, hydrolysis of the COOMe group, amidations of the COOH group, and acylations of the NH2 group. The Structures of pyrazole derivatives were determined by spectroscopic methods and by X-ray diffraction. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.06.021
• 作为产物：
  描述：

  5-[2-(tert-butoxycarbonylamino)ethyl]-1-(4-methoxyphenyl)-1H-pyrazol-4-{N-[2-(ethoxycarbonyl)ethyl]carboxamide} 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 以85%的产率得到5-(2-aminoethyl)-1-(4-methoxyphenyl)-1H-pyrazole-4-{N-[2-(ethoxycarbonyl)ethyl]carboxamide} hydrochloride
  参考文献：
  名称：

  A synthesis of 1-substituted 5-[2-(acylamino)ethyl]-1H-pyrazole-4-carboxamides

  摘要：

  A seven-step synthesis of 1-substituted 5-(2-acylaminoethyl)-1H-pyi-azole-4-carboxamides 20 as the pyrazole analogues of histamine was developed. The synthesis starts with a three-step preparation of N(1)-substituted methyl 5-(2-tert-butoxycarbonylaminoethyl)-1H-pyrazole-4-carboxylates 7 from commercially available Boc-beta-alanine (1). Subsequent four-step transformation of the key-intermediates 7 into the final products 20 was performed following two complementary reaction sequences comprising acidolytic removal of the Boc group, hydrolysis of the COOMe group, amidations of the COOH group, and acylations of the NH2 group. The Structures of pyrazole derivatives were determined by spectroscopic methods and by X-ray diffraction. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.06.021