WAY-100289
Chemical Name: endo-2-(Cyclopropylmethoxy)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylcarbamoyl)benzamide maleate; endo-1-[2-(Cyclopropylmethoxy)benzoyl]-3-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)urea maleate
CAS No. 136013-69-9
项目整合开发状态: Phase I
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:The reaction of salicylamide (I) with cyclopropylmethyl bromide in the presence of potassium hydroxide gives the ether (II).This intermediate is converted to the benzoyl isocyanate (III) by refluxing with oxalyl chloride in 1,2-dichloroethane.The isocyanate is converted without further purification to endo-2-(cyclopropylmethoxy)-N-[[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl) amino]-carbonyl]benzamide (WAY100289) by reaction with endo-3-aminotropane.
📌 参考资料/链接：
参考文献标题:Aroyl-ureas
文献作者:Ward,T.J.; White,J.C.; Bradley,G.(John Wyeth & Brother Ltd.)
参考来源:AU 9163749; EP 0422846; GB 2236528; JP 1991133986
📄 详细内容
合成路线:The reaction of salicylamide (I) with cyclopropylmethyl bromide in the presence of potassium hydroxide gives the ether (II).This intermediate is converted to the benzoyl isocyanate (III) by refluxing with oxalyl chloride in 1,2-dichloroethane.The isocyanate is converted without further purification to endo-2-(cyclopropylmethoxy)-N-[[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl) amino]-carbonyl]benzamide (WAY100289) by reaction with endo-3-aminotropane.
参考文献标题:Novel antagonists of the 5-HT3 receptor.Synthesis and structure activity relationships of (2-alkoxybenzoyl)ureas
文献作者:Bradley,G.; Ward,T.J.; White,J.C.; Coleman,J.; Taylor,A.; Rhodes,K.F.
参考来源:J Med Chem 1992,35(9),1515-9
合成路线:The reaction of salicylamide (I) with cyclopropylmethyl bromide in the presence of potassium hydroxide gives the ether (II).This intermediate is converted to the benzoyl isocyanate (III) by refluxing with oxalyl chloride in 1,2-dichloroethane.The isocyanate is converted without further purification to endo-2-(cyclopropylmethoxy)-N-[[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl) amino]-carbonyl]benzamide (WAY100289) by reaction with endo-3-aminotropane.
参考文献标题:WAY 100289
文献作者:Ward,T.J.
参考来源:Drugs Fut 1993,18(1),23
产品链接: CAS No. 136013-69-9››