Umespirone, KC-9172

3-丁基-7-[4-[4-(2-甲氧基苯基)哌嗪-1-基]丁基]-9,9-二甲基-3,7-二氮杂双环[3.3.1]壬烷-2,4,6,8-四酮Chemical Name: 3-Butyl-7-[4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonan-2,4,6,8-tetraone; N-Butyl-N'-[4-[4-(o-methoxyphenyl)-1-piperazinyl]butyl]-2,2-dimethyl-1,1,3,3-propanetetracarboxylic 1,3:1,3-diimide
CAS No. 107736-98-1
项目整合开发状态: Phase I
项目研究机构: Kali-Chemie (Originator)
合成路线:For the synthesis of umespirone the following synthesis pathway was chosen:Acetone is condensed with ethyl cyanoethanoate (I) to yield ethylisopropylidenecyanoacetate (II).This product is reacted with N-butylcyanoacetamide (III) in sodium methoxide solution to give N-butyl-2,4-dicyano-3,3-dimethylglutarimide (IV).The glutarimide (IV) is cyclized with phosphoric acid to yield 3-butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone (V).The quaternary salt (VIII) (R = CH3),prepared from 1-(2-methoxyphenyl)piperazine (VI) and 1,4-dibromobutane (VII),undergoes reaction with (V) in the presence of potassium carbonate to afford the free base KC-9172 (IX) (R = CH3).