Amotosalen hydrochloride, S-59
7H-呋喃[3,2-g][1]苯并吡喃-7-1,3-[(2-氨基乙氧基)甲基]-2,5,9-三甲基-Chemical Name: 3-(2-Aminoethoxymethyl)-2,5,9-trimethyl-7H-furo[3,2-g]-1-benzopyran-7-one hydrochloride
CAS No. 161262-29-9 (free base)
项目整合开发状态: Pre-Registered
项目研究机构: Cerus (Originator), Baxter (Licensee)
合成路线:Condensation of 7-hydroxy-4,8-dimethylcoumarin (I) with 3-chloro-2-butanone (II) affords the keto alkoxycoumarin (III),which is cyclized to the psoralen derivative (IV) under basic conditions.Benzylic bromination of (IV) by means of N-bromosuccinimide provides the bromomethyl compound (V) as the major isomer.Bromide (V) is then condensed with N-(2-hydroxyethyl)phthalimide (VI) to furnish ether (VII).The phthaloyl group of (VII) is removed by treatment with either primary amines or with hydrazine to produce the target free amine,which is finally isolated as the corresponding hydrochloride salt.
合成路线:A different method starts with the chloromethylation of trimethyl psoralen (I) to afford (II).Subsequent condensation of chloride (II) with ethylene glycol (III) yields the hydroxyethoxy derivative (IV).This is converted to mesylate (V) upon treatment with methanesulfonyl chloride and triethylamine.Mesylate displacement by NaN3 leads to azide (VI).Finally,azide reduction to the target amine is accomplished by treatment with triphenylphosphine in moist THF.
📌 参考资料/链接：
参考文献标题:Cpds.for the photodecontamination of pathogens in blood
文献作者:Wollowitz,S.; Isaacs,S.T.; Rapoport,H.; Spielmann,H.P.(Steritech,Inc.)
参考来源:US 5399719; WO 9500141
📄 详细内容
合成路线:Condensation of 7-hydroxy-4,8-dimethylcoumarin (I) with 3-chloro-2-butanone (II) affords the keto alkoxycoumarin (III),which is cyclized to the psoralen derivative (IV) under basic conditions.Benzylic bromination of (IV) by means of N-bromosuccinimide provides the bromomethyl compound (V) as the major isomer.Bromide (V) is then condensed with N-(2-hydroxyethyl)phthalimide (VI) to furnish ether (VII).The phthaloyl group of (VII) is removed by treatment with either primary amines or with hydrazine to produce the target free amine,which is finally isolated as the corresponding hydrochloride salt.
合成路线:A different method starts with the chloromethylation of trimethyl psoralen (I) to afford (II).Subsequent condensation of chloride (II) with ethylene glycol (III) yields the hydroxyethoxy derivative (IV).This is converted to mesylate (V) upon treatment with methanesulfonyl chloride and triethylamine.Mesylate displacement by NaN3 leads to azide (VI).Finally,azide reduction to the target amine is accomplished by treatment with triphenylphosphine in moist THF.
参考文献标题:Cpds.for the photodecontamination of pathogens in blood
文献作者:Wollowitz,S.; Isaacs,S.T.; Rapoport,H.; Spielman,H.P.; Niero,A.(Steritech,Inc.)
参考来源:WO 9614739
产品链接: CAS No. 161262-29-9››