4-[(2-乙氧基苯甲酰基)氨基]-1-甲基-5-丙基-1H-吡唑-3-甲酰胺 | 501120-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(2-乙氧基苯甲酰基)氨基]-1-甲基-5-丙基-1H-吡唑-3-甲酰胺
• 英文名称: 4-(2-ethoxybenzoyl)amino-1-methyl-5-propyl-3-pyrazolecarboxamide
• 英文别名: 4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide；4-[(2-ethoxybenzoyl)amino]-1-methyl-5-propylpyrazole-3-carboxamide
• CAS: 501120-38-3
• 化学式: C₁₇H₂₂N₄O₃
• 分子量: 330.387
• InChiKey: HFNOLZIPTBNLMC-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192oC
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(2-乙氧基苯甲酰基)氨基]-1-甲基-5-丙基-1H-吡唑-3-甲酰胺 在 氯磺酸 、 PPA 作用下， 反应 1.0h， 生成 去甲基哌嗪基异西地那非磺酰氯
  参考文献：
  名称：

  Synthesis and properties of iso viagra. A 2‐methyl‐2 H ‐pyrazolo[4,3‐ d ]pyrirnidin‐7‐one isomer of viagra ^®

  摘要：

  AbstractThe synthesis and spectral properties (ir, ms, nmr) of a substituted 2‐methyl‐2H‐pyrazolo[4,3‐d]‐pyrimidin‐7‐one (3), an isomer of Viagra®, are described. The key synthon, 4‐amino‐1‐methyl‐5‐propyl‐3‐pyrazolecarboxamide (7), is prepared via the reaction of ethyl 2,4‐dioxoheptanoate with methylhydrazine, followed by cyclization, nitration, amidation, and nitro group reduction. Interaction of 7 with 2‐ethoxyben‐zoyl chloride yielded the respective bis‐amide (8) which was cyclized in polyphosphoric acid to the corresponding pyrazolo[4,3‐d]pyrimidin‐7‐one derivative 9. Chlorosulfonylation of 9, and subsequent treatment with 1‐methylpiperazine furnished iso Viagra (3).

  DOI：

  10.1002/jhet.5570390532
• 作为产物：
  描述：

  1-methyl-4-nitro-5-propyl-3-pyrazolecarboxamide 在 盐酸 、 氯化亚砜 、 水 、 tin(ll) chloride 作用下， 反应 6.0h， 生成 4-[(2-乙氧基苯甲酰基)氨基]-1-甲基-5-丙基-1H-吡唑-3-甲酰胺
  参考文献：
  名称：

  Synthesis and properties of iso viagra. A 2‐methyl‐2 H ‐pyrazolo[4,3‐ d ]pyrirnidin‐7‐one isomer of viagra ^®

  摘要：

  AbstractThe synthesis and spectral properties (ir, ms, nmr) of a substituted 2‐methyl‐2H‐pyrazolo[4,3‐d]‐pyrimidin‐7‐one (3), an isomer of Viagra®, are described. The key synthon, 4‐amino‐1‐methyl‐5‐propyl‐3‐pyrazolecarboxamide (7), is prepared via the reaction of ethyl 2,4‐dioxoheptanoate with methylhydrazine, followed by cyclization, nitration, amidation, and nitro group reduction. Interaction of 7 with 2‐ethoxyben‐zoyl chloride yielded the respective bis‐amide (8) which was cyclized in polyphosphoric acid to the corresponding pyrazolo[4,3‐d]pyrimidin‐7‐one derivative 9. Chlorosulfonylation of 9, and subsequent treatment with 1‐methylpiperazine furnished iso Viagra (3).

  DOI：

  10.1002/jhet.5570390532

文献信息

• Synthesis and properties of <i>iso</i> viagra. A 2‐methyl‐2 <i>H</i> ‐pyrazolo[4,3‐ <i>d</i> ]pyrirnidin‐7‐one isomer of viagra ^®
  作者：Mustafa M. El‐Abadelah、Salim S. Sabri、Monther A. Khanfar、Hani A. Yasin、Wolfgang Voelter

  DOI：10.1002/jhet.5570390532

  日期：2002.9

  AbstractThe synthesis and spectral properties (ir, ms, nmr) of a substituted 2‐methyl‐2H‐pyrazolo[4,3‐d]‐pyrimidin‐7‐one (3), an isomer of Viagra®, are described. The key synthon, 4‐amino‐1‐methyl‐5‐propyl‐3‐pyrazolecarboxamide (7), is prepared via the reaction of ethyl 2,4‐dioxoheptanoate with methylhydrazine, followed by cyclization, nitration, amidation, and nitro group reduction. Interaction of 7 with 2‐ethoxyben‐zoyl chloride yielded the respective bis‐amide (8) which was cyclized in polyphosphoric acid to the corresponding pyrazolo[4,3‐d]pyrimidin‐7‐one derivative 9. Chlorosulfonylation of 9, and subsequent treatment with 1‐methylpiperazine furnished iso Viagra (3).