YM-348
Chemical Name: 1-(7-Ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2(S)-amine; 2-(7-Ethyl-1H-furo[2,3-g]indazol-1-yl)-1(S)-methylethylamine
CAS No. 372163-84-3, 372163-85-4 (succinate)
项目整合开发状态: Preclinical
项目研究机构: Yamanouchi (Originator)
合成路线:The cyclization of 2-ethyl-4,5,6,7-tetrahydrobenzofuran-4-one (I) with ethyl formate and hydrazine by means of tBu-OK in THF gives the furo[2,3-g]indazole derivative (II),which is aromatized by means of DDQ in dioxane,yielding intermediate (III).Finally,this compound is condensed with N-(tert-butoxycarbonyl)-O-(tosyl)-L-alaninol (IV) by means of Cs2CO3 in DMF,followed by a treatment with HCl to afford the target YM-348.Alternatively,intermediate (III) is condensed with (R)-propylene oxide (V) by means of NaH in THF to give the propanol derivative (VI),which is treated first with mesyl chloride and TEA in dichloromethane,and then with Na-N3 in DMF to yield the azide (VII).Finally,this compound is reduced with LiAlH4 in THF to afford the target amine YM-348.
📌 参考资料/链接：
参考文献标题:Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists
文献作者:Maeno,K.; Kazuta,K.; Shimada,I.; et al.
参考来源:224th ACS Natl Meet (Aug 18 2002,Boston) 2002,Abst MEDI 348
📄 详细内容
合成路线:The cyclization of 2-ethyl-4,5,6,7-tetrahydrobenzofuran-4-one (I) with ethyl formate and hydrazine by means of tBu-OK in THF gives the furo[2,3-g]indazole derivative (II),which is aromatized by means of DDQ in dioxane,yielding intermediate (III).Finally,this compound is condensed with N-(tert-butoxycarbonyl)-O-(tosyl)-L-alaninol (IV) by means of Cs2CO3 in DMF,followed by a treatment with HCl to afford the target YM-348.Alternatively,intermediate (III) is condensed with (R)-propylene oxide (V) by means of NaH in THF to give the propanol derivative (VI),which is treated first with mesyl chloride and TEA in dichloromethane,and then with Na-N3 in DMF to yield the azide (VII).Finally,this compound is reduced with LiAlH4 in THF to afford the target amine YM-348.
参考文献标题:Synthesis and structure-activity relationship of a series of indazole derivatives as 5-HT2C receptor agonists
文献作者:Shimada,I.; et al.
参考来源:22nd Symp Med Chem (Nov 27 2002,Shizuoka) 2002,Abst 2P-20
产品链接: CAS No. 372163-84-3››