4-[[5-(4-cyanophenoxy)pentyl]oxy]benzonitrile -Drug Synthesis Database

【结构式】

【分子编号】37312

【品名】4-[[5-(4-cyanophenoxy)pentyl]oxy]benzonitrile

【CA登记号】

【分子式】C₁₉H₁₈N₂O₂

【分子量】306.3642

【元素组成】C 74.49% H 5.92% N 9.14% O 10.44%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

Mitsunobu coupling of 1,5-pentanediol (II) with two molecules of 4-hydroxybenzonitrile (I) in the presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosphine afforded diether (III). Subsequent reduction of the nitrile groups of (III) using LiAlH4 gave the bis(benzylamine) derivative (IV), which was coupled with 3-cyanobenzenesulfonyl chloride (V) to provide sulfonamide (VI). The nitrile groups of (VI) were finally converted to the required bis amidino derivative by treatment with Weinreb reagent, prepared from trimethylaluminum and ammonium chloride.

参考文献中间体

合成目标

【1】 Burgess, L.; Rizzi, J.P. (Array BioPharma, Inc.); Cpds. which inhibit tryptase activity. WO 9924395 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	25109	4-hydroxybenzonitrile	767-00-0	C₇H₅NO	详情	详情
(II)	15471	1,5-pentanediol	111-29-5	C₅H₁₂O₂	详情	详情
(III)	37312	4-[[5-(4-cyanophenoxy)pentyl]oxy]benzonitrile		C₁₉H₁₈N₂O₂	详情	详情
(IV)	37313	[4-([5-[4-(aminomethyl)phenoxy]pentyl]oxy)phenyl]methanamine; 4-([5-[4-(aminomethyl)phenoxy]pentyl]oxy)benzylamine		C₁₉H₂₆N₂O₂	详情	详情
(V)	37314	3-cyanobenzenesulfonyl chloride		C₇H₄ClNO₂S	详情	详情
(VI)	37315	3-cyano-N-[4-([5-[4-([[(3-cyanophenyl)sulfonyl]amino]methyl)phenoxy]pentyl]oxy)benzyl]benzenesulfonamide		C₃₃H₃₂N₄O₆S₂	详情	详情

Extended Information