GMC-1111
N6,N6-二丙基-6,7-二氢-5H-茚[5,6-d][1,3]噻唑-2,6-二胺 5H-茚(5,6-d)噻唑-2,6-二胺,6,7-二氢氮-N6,N6-二丙基-,二盐酸盐 Chemical Name: N6,N6-Dipropyl-6,7-dihydro-5H-indeno[5,6-d][1,3]thiazole-2,6-diamine; N-(2-Amino-6,7-dihydro-5H-indeno[5,6-d][1,3]thiazol-6-yl)-N,N-dipropylamine
CAS No. 254885-67-1, 254885-69-3 (diHCl)
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator), Rijksuniversiteit Groningen (Originator)
合成路线:After acylation of 2-aminoindan (I) with propionyl chloride,the resulting propionamide (II) was reduced with borane to the amine (III).Further acylation of (III) with propionyl chloride furnished amide (IV).Nitration of (IV),followed by transfer hydrogenation of nitro derivative (V),gave rise to aniline (VI).Reduction of the amide function of (VI) with borane yielded diamine (VII).Subsequent reaction of aniline (VII) with thiocyanogen,generated from KSCN and Br2,provided the desired benzothiazole along with the regioisomeric analogue (VIII),which were separated by column chromatography.
📌 参考资料/链接：
参考文献标题:New 2-aminothiazol-fused-2-aminoindans and 2-aminotetralins and their use
文献作者:Van Vliet,L.A.; Wikstr鰉,H.V.; Dukstra,D.; Gunne,L.; Carlsson,P.A.E.; Andr閚,P.E.
参考来源:WO 0001680
📄 详细内容
合成路线:After acylation of 2-aminoindan (I) with propionyl chloride,the resulting propionamide (II) was reduced with borane to the amine (III).Further acylation of (III) with propionyl chloride furnished amide (IV).Nitration of (IV),followed by transfer hydrogenation of nitro derivative (V),gave rise to aniline (VI).Reduction of the amide function of (VI) with borane yielded diamine (VII).Subsequent reaction of aniline (VII) with thiocyanogen,generated from KSCN and Br2,provided the desired benzothiazole along with the regioisomeric analogue (VIII),which were separated by column chromatography.
参考文献标题:Thiazoloindans and thiazolobenzopyrans: A novel class of orally active central dopamine (partial) agonists
文献作者:van Vliet,L.A.; Rodenhuis,N.; Wikstr鰉,H.; Pugsley,T.A.; Serpa,K.A.; Meltzer,L.T.; Heffner,T.G.; Wise,L.D.; Lajiness,M.E.; Huff,R.M.; Svensson,K.; Haenen,G.R.; Bast,A.
参考来源:J Med Chem 2000,43(19),3549
产品链接: CAS No. 254885-67-1›› 产品链接: CAS No.254885-69-3››