6-(N,N-diethylcarboxamido)-2-methoxy-N-(2-phenylpropan-2-yl)benzenesulfonamide | 936841-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(N,N-diethylcarboxamido)-2-methoxy-N-(2-phenylpropan-2-yl)benzenesulfonamide
• 英文别名: N,N-diethyl-3-methoxy-2-[(1-methyl-1-phenylethyl)sulfamoyl]benzamide；N,N-diethyl-3-methoxy-2-(2-phenylpropan-2-ylsulfamoyl)benzamide
• CAS: 936841-26-8
• 化学式: C₂₁H₂₈N₂O₄S
• 分子量: 404.53
• InChiKey: QXJDLNOLIRMDAT-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C(Solv: hexane (110-54-3))
• 沸点：
  582.9±60.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(N,N-diethylcarboxamido)-2-methoxy-N-(2-phenylpropan-2-yl)benzenesulfonamide 在 正丁基锂 、 四甲基乙二胺 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以62%的产率得到6-(N,N-diethylcarboxamido)-5-iodo-2-methoxy-N-(2-phenylpropan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Directed Ortho Metalation−Cross Coupling Strategies. N-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins

  摘要：

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).

  DOI：

  10.1021/jo062385v
• 作为产物：
  描述：

  2-苯基-2-丙醇 在 Lindlar's catalyst 正丁基锂 、 sodium azide 、 四甲基乙二胺 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 25.0h， 生成 6-(N,N-diethylcarboxamido)-2-methoxy-N-(2-phenylpropan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Directed Ortho Metalation−Cross Coupling Strategies. N-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins

  摘要：

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).

  DOI：

  10.1021/jo062385v

文献信息

• [EN] NEW COMPOUNDS INHIBITORS OF THE YAP/TAZ-TEAD INTERACTION AND THEIR USE IN THE TREATMENT OF MALIGNANT MESOTHELIOMA<br/>[FR] NOUVEAUX COMPOSÉS INHIBITEURS DE L'INTERACTION YAP/TAZ-TEAD ET LEUR UTILISATION DANS LE TRAITEMENT DU MÉSOTHÉLIOME MALIN
  申请人：INVENTIVA

  公开号：WO2017064277A1

  公开（公告）日：2017-04-20

  The invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5 and R6 are as defined in the description. The compounds of formula (I) are inhibitors of the YAP/TAZ-TEAD interaction.

  该发明涉及公式（I）中的化合物，其中R1、R2、R3、R4、R5和R6如描述中所定义。公式（I）中的化合物是YAP/TAZ-TEAD相互作用的抑制剂。
• NEW COMPOUNDS INHIBITORS OF THE YAP/TAZ-TEAD INTERACTION AND THEIR USE IN THE TREATMENT OF MALIGNANT MESOTHELIOMA
  申请人：INVENTIVA

  公开号：EP3156404A1

  公开（公告）日：2017-04-19

  The invention relates to compounds of formula I wherein R1, R2, R3, R4, R5 are as defined in the description. The compounds of formula I are useful for the treatment of diseases where inhibition of the YAP/TAZ-TEAD interaction is required.

  本发明涉及式 I 的化合物 其中 R1、R2、R3、R4、R5 如描述中所定义。 式 I 的化合物可用于治疗需要抑制 YAP/TAZ-TEAD 相互作用的疾病。
• Compounds as inhibitors of the YAP/TAZ-TEAD interaction and their use in the treatment of malignant mesothelioma
  申请人：INVENTIVA

  公开号：US10414739B2

  公开（公告）日：2019-09-17

  The invention relates to compounds of formula (I): wherein R1, R2, R3, R4, R5 and R6 are as defined in the description. The compounds of formula (I) are inhibitors of the YAP/TAZ-TEAD interaction.

  本发明涉及式 (I) 化合物： 其中 R1、R2、R3、R4、R5 和 R6 如说明中所定义。 式（I）化合物是 YAP/TAZ-TEAD 相互作用的抑制剂。