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【结 构 式】 
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【分子编号】37315 【品名】3-cyano-N-[4-([5-[4-([[(3-cyanophenyl)sulfonyl]amino]methyl)phenoxy]pentyl]oxy)benzyl]benzenesulfonamide 【CA登记号】 |
【 分 子 式 】C33H32N4O6S2 【 分 子 量 】644.77244 【元素组成】C 61.47% H 5% N 8.69% O 14.89% S 9.95% |
合成路线1
该中间体在本合成路线中的序号：(VI)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.
| 【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 |