ethyl 1-ethyl-3-methyl-1H-pyrazole-4-carboxylate | 1451192-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-ethyl-3-methyl-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 1-ethyl-3-methylpyrazole-4-carboxylate
• CAS: 1451192-48-5
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: XVRCMCUXKFZVGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 在 乙酸酐 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 ethyl 1-ethyl-3-methyl-1H-pyrazole-4-carboxylate 、 ethyl 1-ethyl-5-methyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Convergent and streamlined synthesis of 6-etherified imidazo[1,2-b]pyridazine-2-amine derivatives possessing VEGFR-2 kinase inhibitory activity

  摘要：

  A convergent and streamlined synthesis of selective vascular endothelial growth factor receptor (VEGFR) 2 kinase inhibitors has been achieved using a synthetic strategy based on an SNAr reaction of 6-chloroimidazo[1,2-b]pyridazine with phenols in the final step. For the synthesis of 6-chloroimidazo[1,2-b]pyridazine, a one-pot reaction using 3-amino-6-chloropyridazine, cyclopropanecarboxamide, and bromoacetyl bromide was developed. The phenols were easily prepared by chemoselective acylation of 3-aminophenols with pyrazole carboxylic acids, and an efficient and high-yielding synthesis of N-ethylpyrazole was also developed. The SNAr reaction of 6-chloroimidazo[1,2-b]pyridazine with phenols in DMSO in the presence of cesium carbonate successfully proceeded at 100-110 degrees C to give the target products in good yields. This new chromatography-free process will be not only useful for the further bulk supply of these compounds but also applicable to the synthesis of other compounds containing the 6-etherified imidazo[1,2-b]pyridazin-2-amine core. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.087

文献信息

• [EN] BENZODIAZEPINE DERIVATIVES FOR TREATING A RESPIRATORY SYNCYTIAL VIRUS (RSV) INFECTION<br/>[FR] DÉRIVÉS DE BENZODIAZÉPINE POUR LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS RESPIRATOIRE SYNCYTIAL (RSV)
  申请人：REVIRAL LTD

  公开号：WO2021079121A1

  公开（公告）日：2021-04-29

  Benzodiazepine derivatives of formula (I): wherein: each of R1 and R2 is independently H or halo; R3 is H, C1-C6 alkyl, -NHR8 or -OR'; either (i) a, c, and e are all bonds, with b, d and f absent; or b, d and f are all bonds, with a, c and e absent; R4 is H or a group selected from C1-C6 alkyl, C3-C6 cycloalkyl and 4- to 10-membered heterocyclyl, the group being unsubstituted or substituted; R5 is H or halo; R6 is -OR8, -NR8R9 or -R8; R7 is H or halo; each of R8 and R9 is independently H or a group selected from C1-C6 alkyl, C3-C6 cycloalkyl and 4- to 10-membered heterocyclyl, the group being unsubstituted or substituted; R' is H or C1-C6 alkyl; and one of V and W is CH and the other is N or CH; and the pharmaceutically acceptable salts thereof are inhibitors of RSV and can therefore be used to treat or prevent an RSV infection.

  苯二氮卓啉衍生物的结构式（I）：其中：R1和R2中的每一个独立地是H或卤素；R3是H，C1-C6烷基，-NHR8或-OR'；要么（i）a，c和e都是键，b，d和f不存在；要么b，d和f都是键，a，c和e不存在；R4是H或从C1-C6烷基，C3-C6环烷基和4-到10-成员杂环基中选择的基团，该基团未取代或取代；R5是H或卤素；R6是-OR8，-NR8R9或-R8；R7是H或卤素；R8和R9中的每一个独立地是H或从C1-C6烷基，C3-C6环烷基和4-到10-成员杂环基中选择的基团，该基团未取代或取代；R'是H或C1-C6烷基；V和W中的一个是CH，另一个是N或CH；以及其药用盐是RSV的抑制剂，因此可用于治疗或预防RSV感染。
• BENZODIAZEPINE DERIVATIVES FOR TREATING A RESPIRATORY SYNCYTIAL VIRUS (RSV) INFECTION
  申请人：Reviral Limited

  公开号：EP4048665A1

  公开（公告）日：2022-08-31
• Convergent and streamlined synthesis of 6-etherified imidazo[1,2-b]pyridazine-2-amine derivatives possessing VEGFR-2 kinase inhibitory activity
  作者：Kazuhisa Ishimoto、Yasuhiro Sawai、Naohiro Fukuda、Toshiaki Nagata、Tomomi Ikemoto

  DOI：10.1016/j.tet.2013.07.087

  日期：2013.10

  A convergent and streamlined synthesis of selective vascular endothelial growth factor receptor (VEGFR) 2 kinase inhibitors has been achieved using a synthetic strategy based on an SNAr reaction of 6-chloroimidazo[1,2-b]pyridazine with phenols in the final step. For the synthesis of 6-chloroimidazo[1,2-b]pyridazine, a one-pot reaction using 3-amino-6-chloropyridazine, cyclopropanecarboxamide, and bromoacetyl bromide was developed. The phenols were easily prepared by chemoselective acylation of 3-aminophenols with pyrazole carboxylic acids, and an efficient and high-yielding synthesis of N-ethylpyrazole was also developed. The SNAr reaction of 6-chloroimidazo[1,2-b]pyridazine with phenols in DMSO in the presence of cesium carbonate successfully proceeded at 100-110 degrees C to give the target products in good yields. This new chromatography-free process will be not only useful for the further bulk supply of these compounds but also applicable to the synthesis of other compounds containing the 6-etherified imidazo[1,2-b]pyridazin-2-amine core. (C) 2013 Elsevier Ltd. All rights reserved.