N-(N,N-dimethylaminoethylamine)-4-nitro-2-methoxybenzamide | 617244-33-4

• 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: N-(N,N-dimethylaminoethylamine)-4-nitro-2-methoxybenzamide
• 英文别名: N-(N,N-dimethylaminoethyl)-4-nitro-2-methoxybenzoic amide；N-[2-(dimethylamino)ethyl]-2-methoxy-4-nitrobenzamide
• CAS: 617244-33-4
• 化学式: C₁₂H₁₇N₃O₄
• 分子量: 267.285
• InChiKey: DVYPNKJPRQXPGH-UHFFFAOYSA-N

物化性质

• 沸点：
  431.8±45.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N,N-dimethylaminoethylamine)-4-nitro-2-methoxybenzamide 在 钯 氢气 、 crude product 、 Al2O3 、 Ammonia methanol dichloromethane 作用下， 以 乙醇 为溶剂， 以giving 0.42 g (95%) of the title product的产率得到4-amino-N-(2-dimethylamino-ethyl)-2-methoxy-benzamide
  参考文献：
  名称：

  Novel methoxybenzamibe compounds for use in mch receptor related disorders

  摘要：

  本发明揭示了式（I）的新化合物，其调节MCH活性，其中A是连接剂；Ar1是芳基或杂环芳基基团；R1是较低的烷氧基团；R2是R1基团或氢、OH或NH2基团，Q与羰基一起形成酰胺基团，该酰胺基团进一步被取代为胺基团；R5选自氢、卤原子、烷氧基团、羟基、烷基氨基基团、二烷基氨基基团、羟基烷基基团、羧酰胺基团、酰胺基团、酰基、—CHO、腈、烷基、烯基或炔基基团、—SCH3、部分或完全氟化的烷基、烷氧基或硫代烷氧基团，如—CH2CF3、—CF2CF3、—CF3、—OCF3、—SCF3；—SO2NH2、—SO2NHAlk、—SO2NAlk2、—SO2Alk；X是H、F、Cl、Br、I、—SCH3、—CF3、—OCF3、—SCF3、OCH3或较低的烷基或烯基基团；R8是卤原子、烷基、烯基或炔基基团、环烷基基团、芳基基团、杂环芳基基团、烷基环烷基基团、烷基芳基基团、烷基杂环芳基基团、芳基烷氧基团、芳氧基团、烷氧基团、二烷基氨基基团、—CONHAlk、—CONHAr、—CONAlk2、—NHCO-Alk、—NHCO—Ar、—CO-Alk、—CO—Ar、—SCH3、部分或完全氟化的烷基、烷氧基或硫代烷氧基；或R8是R6-Ar2—B—，其中B是单键或连接基；Ar2是Ar1基团；R6是R5基团；并且这些化合物在治疗或预防肥胖症、抑郁症、糖尿病、贪食症等方面是有用的。

  公开号：

  US20060235035A1
• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 potassium cyanate 、 copper (II) carbonate hydroxide 、 乌洛托品 、 氧气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 N-(N,N-dimethylaminoethylamine)-4-nitro-2-methoxybenzamide
  参考文献：
  名称：

  使用铜催化剂对芳基 C(sp2)-H 键进行药物导向的甲氧基化

  摘要：

  已开发出一种以药物为导向、铜 (II) 催化的芳基 C(sp2)-H 键甲氧基化。这种简单且环境友好的反应体系使用氧气作为氧化剂有效地发生，具有广泛的底物范围和高官能团耐受性。

  DOI：

  10.1055/s-0037-1610132

文献信息

• [EN] NOVEL BENZAMIDE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS<br/>[FR] NOUVEAUX COMPOSES DE BENZAMIDE DESTINES A ETRE UTILISES DANS DES TROUBLES ASSOCIES AU RECEPTEUR DE MCH
  申请人：7TM PHARMA AS

  公开号：WO2004048319A1

  公开（公告）日：2004-06-10

  Novel compounds of Formula I which modulate MCH activity are disclosed, in which A is a linker, Ar, is an aryl or heteroaryl group; R1 is hydrogen or a lower alkoxy group; Q together with the carbonyl forms an amide group, which is further substituted with an amine group; R5 is hydrogen, halogen atoms, alkoxy groups, hydroxy, alkylamino groups, dialkylamino groups, hydroxylalkyl groups, carboxamido groups, acylamido groups, acyl groups, -CHO, nitrile, alkyl, alkenyl or alkynyl groups, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, -CF2CF3, -CF3, -OCF3, -SCF3; -SO2NH2, -SO2NHAlk, -SO2NAlk2, -SO2AIk; R8 is hydrogen, halogen atoms, alkyl, alkenyl or alkynyl groups, cycloalkyl groups, alkylcycloalkyl groups, alkoxy groups, dialkylamino groups, -CONHAIk, -CONAIk2, - NHCO-Alk, -CO-Alk, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, -CF2CF3, -CF3, -OCF3, -SCF3; X is H, F, Cl, Br, I, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, - CF2CF3, -CF3, -OCF3, -SCF3; OCH3 or lower alkyl or alkenyl group; and which are useful in the treatment or prevention of e.g. obesity, depression, diabetes, bulimia etc.

  公开了调节MCH活性的Formula I的新化合物，其中A是连接剂，Ar是芳基或杂环芳基；R1是氢或较低的烷氧基；Q与羰基一起形成酰胺基团，该基团进一步被氨基取代；R5是氢、卤素原子、烷氧基、羟基、烷基氨基基团、二烷基氨基基团、羟基烷基基团、羧酰胺基团、酰胺基团、酰基、-CHO、腈基、烷基、烯基或炔基、-SCH3、部分或完全氟代烷基、烷氧基或硫代烷氧基基团，如-CH2CF3、-CF2CF3、-CF3、-OCF3、-SCF3；-SO2NH2、-SO2NHAlk、-SO2NAlk2、-SO2AIk；R8是氢、卤素原子、烷基、烯基或炔基、环烷基、烷基环烷基、烷氧基、二烷基氨基基团、-CONHAIk、-CONAIk2、-NHCO-Alk、-CO-Alk、-SCH3、部分或完全氟代烷基、烷氧基或硫代烷氧基基团，如-CH2CF3、-CF2CF3、-CF3、-OCF3、-SCF3；X是H、F、Cl、Br、I、-SCH3、部分或完全氟代烷基、烷氧基或硫代烷氧基基团，如-CH2CF3、-CF2CF3、-CF3、-OCF3、-SCF3；OCH3或较低的烷基或烯基基团；这些化合物在治疗或预防肥胖、抑郁症、糖尿病、暴食症等方面是有用的。
• [EN] NOVEL METHOXYBENZAMIDE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS<br/>[FR] NOUVEAUX COMPOSES DE METHOXYBENZAMIDE DESTINES A ETRE UTILISES DANS LE TRAITEMENT DES TROUBLES LIES AU RECEPTEUR DE MCH
  申请人：7TM PHARMA AS

  公开号：WO2003087045A1

  公开（公告）日：2003-10-23

  Novel compounds of Formula (I) which modulate MCH activity are disclosed, in which A is a linker; Ar1 is an aryl or heteroaryl group; R1 is a lower alkoxy group; R2 is an R1 group or hydrogen, an OH or an NH2 group, Q together with the carbonyl forms an amide group, which is further substituted with an amine group; R5 is selected from hydrogen, halogen atoms, alkoxy groups, hydroxy, alkylamino groups, dialkylamino groups, hydroxylalkyl groups, carboxamido groups, acylamido groups, acyl groups, -CHO, nitrile, alkyl, alkenyl or alkynyl groups, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, -CF2CF3, -CF3, -OCF3, -SCF3; -SO2NH2, -SO2NHAlk, -SO2NAlk2, -SO2Alk; X is H, F, Cl, Br, I, -SCH3, -CF3, -OCF3, -SCF3, OCH3, or lower alkyl or alkenyl group; R8 is halogen atoms, alkyl, alkenyl or alkynyl groups, cycloalkyl groups, aryl groups, heteroaryl groups, heterocyclyl groups, alkylcycloalkyl groups, alkylaryl groups, alkylheterocyclyl groups, alkylheteroaryl groups, arylalkoxy groups, aryloxy groups, alkoxy groups, dialkylamino groups, -CONHAlk, -CONHAr, -CONAlk2, -NHCO-Alk, -NHCO-Ar, -CO-Alk, -CO-Ar, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups; or R8 is R6-Ar2-B-, in which B is a single bond or a connecting moiety; Ar2 is an Ar1 group; R6 is an R5 group; and which are useful in the treatment or prevention of e.g. obesity, depression, diabetes, bulimia etc.

  化合物的新颖化合物的公式（I），其调节MCH活性，其中A是连接剂；Ar1是芳基或杂芳基；R1是较低的烷氧基团；R2是R1基团或氢，OH或NH2基团，Q与羰基一起形成酰胺基团，该基团进一步被氨基团取代；R5从氢，卤素原子，烷氧基团，羟基，烷基氨基团，二烷基氨基团，羟基烷基基团，羧酰胺基团，酰胺基团，酰基，-CHO，腈，烷基，烯基或炔基团，-SCH3，部分或完全氟化的烷基，烷氧基或硫代烷氧基团，如-CH2CF3，-CF2CF3，-CF3，-OCF3，-SCF3；-SO2NH2，-SO2NHAlk，-SO2NAlk2，-SO2Alk；X是H，F，Cl，Br，I，-SCH3，-CF3，-OCF3，-SCF3，OCH3，或较低的烷基或烯基基团；R8是卤素原子，烷基，烯基或炔基团，环烷基团，芳基，杂芳基，杂环烷基团，烷基环烷基团，烷基芳基团，烷基杂环烷基团，烷基杂芳基团，芳基烷氧基团，芳氧基团，烷氧基团，二烷基氨基团，-CONHAlk，-CONHAr，-CONAlk2，-NHCO-Alk，-NHCO-Ar，-CO-Alk，-CO-Ar，-SCH3，部分或完全氟化的烷基，烷氧基或硫代烷氧基团；或R8是R6-Ar2-B-，其中B是单键或连接基；Ar2是Ar1基团；R6是R5基团；在治疗或预防肥胖，抑郁症，糖尿病，暴食症等方面是有用的。
• 一种药物官能团应用于C-H甲氧基化制备芳 香醚的方法
  申请人：浙江工业大学

  公开号：CN108456146B

  公开（公告）日：2020-12-25

  本发明公开了一种药物官能团应用于C‑H甲氧基化制备芳香醚的方法：以式(I)所示的芳香甲酰胺衍生物为原料，在铜催化剂、添加剂乌洛托品的作用下，以甲醇为有机溶剂，60～120℃的反应温度下，氧气或空气的气氛下密闭搅拌反应12h～24h，制得式(II)所示的芳香甲酰胺衍生物产物。本发明应用C‑H活化的方法通过简单的反应直接得到芳香醚，符合原子经济性的考量，同时使用氧气和空气等清洁试剂作为氧化剂，减少了不利于坏境的副产物的产生。
• Pharmaceutical-Oriented Methoxylation of Aryl C(sp2)–H Bonds using Copper Catalysts
  作者：Chengrong Ding、Guofu Zhang、Jianfei Zhu、Chaolai Tong

  DOI：10.1055/s-0037-1610132

  日期：2018.7

  A pharmaceutical-oriented, copper(II)-catalyzed methoxylation of aryl C(sp2)–H bonds has been developed. This simple and environmentally benign reaction system occurs efficiently using oxygen as oxidant with broad substrate scope and high functional group tolerance.

  已开发出一种以药物为导向、铜 (II) 催化的芳基 C(sp2)-H 键甲氧基化。这种简单且环境友好的反应体系使用氧气作为氧化剂有效地发生，具有广泛的底物范围和高官能团耐受性。
• Novel methoxybenzamibe compounds for use in mch receptor related disorders
  申请人：Hogberg Thomas

  公开号：US20060235035A1

  公开（公告）日：2006-10-19

  Novel compounds of Formula (I) which modulate MCH activity are disclosed, in which A is a linker; Ar 1 is an aryl or heteroaryl group; R1 is a lower alkoxy group; R2 is an R1 group or hydrogen, an OH or an NH 2 group, Q together with the carbonyl forms an amide group, which is further substituted with an amine group; R5 is selected from hydrogen, halogen atoms, alkoxy groups, hydroxy, alkylamino groups, dialkylamino groups, hydroxylalkyl groups, carboxamido groups, acylamido groups, acyl groups, —CHO, nitrile, alkyl, alkenyl or alkynyl groups, —SCH 3 , partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as —CH 2 CF 3 , —CF 2 CF 3 , —CF 3 , —OCF 3 , —SCF 3 ; —SO 2 NH 2 , —SO 2 NHAlk, —SO 2 NAlk 2 , —SO 2 Alk; X is H, F, Cl, Br, I, —SCH 3 , —CF 3 , —OCF 3 , —SCF 3 , OCH 3 , or lower alkyl or alkenyl group; R8 is halogen atoms, alkyl, alkenyl or alkynyl groups, cycloalkyl groups, aryl groups, heteroaryl groups, heterocyclyl groups, alkylcycloalkyl groups, alkylaryl groups, alkylheterocyclyl groups, alkylheteroaryl groups, arylalkoxy groups, aryloxy groups, alkoxy groups, dialkylamino groups, —CONHAlk, —CONHAr, —CONAlk 2 , —NHCO-Alk, —NHCO—Ar, —CO-Alk, —CO—Ar, —SCH 3 , partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups; or R8 is R6-Ar 2 —B—, in which B is a single bond or a connecting moiety; Ar 2 is an Ar 1 group; R6 is an R5 group; and which are useful in the treatment or prevention of e.g. obesity, depression, diabetes, bulimia etc.

  本发明揭示了式（I）的新化合物，其调节MCH活性，其中A是连接剂；Ar1是芳基或杂环芳基基团；R1是较低的烷氧基团；R2是R1基团或氢、OH或NH2基团，Q与羰基一起形成酰胺基团，该酰胺基团进一步被取代为胺基团；R5选自氢、卤原子、烷氧基团、羟基、烷基氨基基团、二烷基氨基基团、羟基烷基基团、羧酰胺基团、酰胺基团、酰基、—CHO、腈、烷基、烯基或炔基基团、—SCH3、部分或完全氟化的烷基、烷氧基或硫代烷氧基团，如—CH2CF3、—CF2CF3、—CF3、—OCF3、—SCF3；—SO2NH2、—SO2NHAlk、—SO2NAlk2、—SO2Alk；X是H、F、Cl、Br、I、—SCH3、—CF3、—OCF3、—SCF3、OCH3或较低的烷基或烯基基团；R8是卤原子、烷基、烯基或炔基基团、环烷基基团、芳基基团、杂环芳基基团、烷基环烷基基团、烷基芳基基团、烷基杂环芳基基团、芳基烷氧基团、芳氧基团、烷氧基团、二烷基氨基基团、—CONHAlk、—CONHAr、—CONAlk2、—NHCO-Alk、—NHCO—Ar、—CO-Alk、—CO—Ar、—SCH3、部分或完全氟化的烷基、烷氧基或硫代烷氧基；或R8是R6-Ar2—B—，其中B是单键或连接基；Ar2是Ar1基团；R6是R5基团；并且这些化合物在治疗或预防肥胖症、抑郁症、糖尿病、贪食症等方面是有用的。