S-34324
Chemical Name: 4-(5-Fluoroindan-2-ylmethyl)-4,5-dihydro-1H-imidazole
CAS No. 276235-47-3
项目整合开发状态: Preclinical
项目研究机构: Servier (Originator)
合成路线:2-(Hydroxymethyl)-5-fluoroindane (I) was converted to bromide (II) upon treatment with CBr4 and PPh3.Alkylation of N-(diphenylmethylene)aminoacetonitrile (III) with bromide (II) under phase-transfer conditions furnished amino nitrile (V),which was reduced to diamine (VI) by using LiAlH4 in THF.Finally,condensation of diamine (V) with formamidine acetate yielded the target imidazoline.
📌 参考资料/链接：
参考文献标题:Imidazoline derivs.,preparation and pharmaceutical compsns.containing them
文献作者:Newman-Tancredi,A.; Lacoste,J.-M.; Millan,M.; Cordi,A.; Gobert,A.(ADIR et Cie.)
参考来源:EP 1010693; FR 2787451; JP 2000178255; US 6127396
📄 详细内容
合成路线:In an alternative procedure,Wadsworth-Emmons condensation of 5-fluoroindan-2-one (VI) with triethyl phosphonoacetate gave the indeneacetate (VII),which was reduced to aldehyde (VIII) employing diisobutylaluminum hydride.Strecker reaction of aldehyde (VIII) with NaCN and NH-4-Cl produced amino nitrile (IX).This was reduced to diamine (X) using LiAlH4,and then condensed with formamidine acetate to produce imidazoline (XI).Finally,catalytic hydrogenation of indene (XI) over Pd/C provided the title indane derivative.
参考文献标题:Potential antidepressants displayed combined alpha2-adrenoceptor antagonist and monoamine uptake inhibitor properties
文献作者:Cordi,A.A.; Berque-Bestel,I.; Persigand,T.; Lacoste,J.-M.; Newman-Tancredi,A.; Audinot,V.; Millan,M.J.
参考来源:J Med Chem 2001,44(5),787
产品链接: CAS No. 276235-47-3››