4-<<(2-Amino-3-pyridinyl)amino>methyl>-N-cyclohexyl-3-methoxy-N-(1-methylethyl)benzamide

• 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: 4-<<(2-Amino-3-pyridinyl)amino>methyl>-N-cyclohexyl-3-methoxy-N-(1-methylethyl)benzamide
• 英文别名: N-cyclohexyl-3-methoxy-4-[((2-amino-3-pyridinyl)amino)methyl]-N-(1methylethyl)benzamide；4-[[(2-aminopyridin-3-yl)amino]methyl]-N-cyclohexyl-3-methoxy-N-propan-2-ylbenzamide
• 化学式: C₂₃H₃₂N₄O₂
• 分子量: 396.533
• InChiKey: GDOBDXBOLHDHKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二氨基吡啶 、 4-formyl-3-methoxybenzoic acid N-isopropyl-N-cyclohexyl amide 在 sodium tetrahydroborate 、 4 A molecular sieve 作用下， 生成 4-<<(3-Amino-2-pyridinyl)amino>methyl>-N-cyclohexyl-3-methoxy-N-(1-methylethyl)benzamide 、 4-<<(2-Amino-3-pyridinyl)amino>methyl>-N-cyclohexyl-3-methoxy-N-(1-methylethyl)benzamide
  参考文献：
  名称：

  Facile, Regioselective Syntheses of N-Alkylated 2,3-Diaminopyridines and Imidazo[4,5-b]pyridines

  摘要：

  Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to give predominantly the N-3 alkylated products, which have been used for the regioselective synthesis of N-1 substituted imidazo[4,5-b]pyridines. Investigations using 2-formamido-3-aminopyridine (13), synthesized in two steps from 2-amino-3-nitropyridine, show it to be a versatile intermediate for the regioselective synthesis of either N-1 or N-3 substituted imidazo[4,5-b]pyridines, depending upon the conditions employed. The reductive amination of aldehydes with 13 using borane-pyridine in acetic acid affords the N-1 substituted imidazo[4,5-b]pyridines in one step, whereas reaction of 13 with alkyl halides in the presence of a suitable base (e.g., cesium carbonate) yields the N-3 substituted imidazo[4,5-b]pyridines. The generality of this synthetic methodology is noted.

  DOI：

  10.1021/jo00109a029

文献信息

• SUBSTITUTED-PHENYL(N,N'-CYCLOALKYL/ALKYL CARBOXAMIDE)-1H/3H-IMIDAZO 4,5-b]PYRIDINE COMPOUNDS AS PAF ANTAGONISTS
  申请人：G.D. SEARLE & CO.

  公开号：EP0670838A1

  公开（公告）日：1995-09-13
• US5359073A
  申请人：——

  公开号：US5359073A

  公开（公告）日：1994-10-25
• [EN] SUBSTITUTED-PHENYL(N,N'-CYCLOALKYL/ALKYL CARBOXAMIDE)-1H/3H-IMIDAZO[4,5-b]PYRIDINE COMPOUNDS AS PAF ANTAGONISTS<br/>[FR] COMPOSES DE N,N'-CYCLOALKYL/ALKYLCARBOXIMIDE (A PHENYL SUBSTITUE) 1H/3H-IMIDAZO[4,5-b]PYRIDINE EN TANT QU'ANTAGONISTES DU FACTEUR PLAQUETTAIRE
  申请人：——

  公开号：WO1994012500A1

  公开（公告）日：1994-06-09

  [EN] A class of N,N'-cycloalkyl/alkyl benzamides of certain 1H-imidazo[4,5-b]pyridine and 3H-imidazo[4,5-b]pyridine compounds is described for treating cardiovascular and immuno-inflammatory related disorders mediated by platelet activating factor (PAF). Compounds of particular interest are those of formula (I), wherein each of X and X is independently selected from nitrogen atom and -CH-, with the proviso that when one of X and X is selected as nitrogen atom, then the other of X and X must be -CH-; wherein R<1> is selected from hydrido, alkyl, hydroxyalkyl, alkoxyalkyl, phenyl, halophenyl, alkylsilyloxyalkyl, amino, monoalkylamino, dialkylamino, aminoalkyl, monoalkylaminoalkyl and dialkylaminoalkyl; wherein each of R<5>, R<6>, R<7> and R<8> is independently selected from hydrido, hydroxy, alkyl, alkoxy, fluoro, chloro, bromo, haloalkyl, alkylthio, alkoxyalkyl, hydroxyalkyl, alkylthioalkyl, cyano, amino, monoalkylamino and dialkylamino; wherein each of R<9> and R<10> is independently selected from hydrido, alkyl, cycloalkyl, bicycloalkyl, heteroaryl, aryl, alkenyl and cycloalkenyl, and wherein any of said R<9> and R<10> substituents may be further substituted with one or more groups selected from linear or branched lower alkyl, lower alkoxy, fluoro, chloro and bromo; or a pharmaceutically-acceptable salt thereof.
  [FR] L'invention concerne une classe de benzoamides de N,N'-cycloalkyl/alkyle de certains composés de 1H-imidazo[4,5-b]pyridine et de 3H-imidazo[4,5-b]pyridine destinés à traiter les troubles cardiovasculaires et immuno-inflammatoires transmis par le facteur plaquettaire. Les composés selon l'invention sont représentés par la formule (I), dans laquelle Xa et Xb représentent indépendamment un atome d'azote ou -CH-, à condition que lorsque Xa représente un atome d'azote, Xb représente -CH- et inversement; R1 est sélectionné parmi hydrido, alkyle, hydroxyalkyle, alcoxyalkyle, phényle, halophényle, alkylsilyloxyalkyle, amino, monoalkylamino, dialkylamino, aminoalkyle, monoalkylaminoalkyle et dialkylaminoalkyle, R5, R6, R7 et R8 sont sélectionnés indépendamment l'un de l'autre parmi hydrido, hydroxy, alkyle, alcoxy, fluoro, chloro, bromo, haloalkyle, alkylthio, alcoxyalkyle, hydroxyalkyle, alkylthioalkyle, cyano, amino, monoalkylamino et dialkylamino; R9 et R10 sont sélectionnés indépendamment parmi hydrido, alkyle, cycloalkyle, bicycloalkyle, hétéroaryle, aryle, alcényle et cycloalcényle, chacun desdits substituants R9 et R10 pouvant être encore substitué par un ou plusieurs groupes sélectionnés parmi alkyle inférieur, alcoxy inférieur, fluoro, chloro et bromo à chaîne droite ou ramifiée. L'invention concerne également un sel pharmaceutiquement acceptable dérivé de ces composés.