WAY-132983

Chemical Name: (3R,4R)-3-[3-(Hexylsulfanyl)pyrazin-2-yloxy]-1-azabicyclo[2.2.1]heptane hydrochloride
项目整合开发状态: Preclinical
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:The reaction of 2,3-dichloropyrazine (I) with hexanethiol (II) by means of NaH in DMF/THF gives 2-chloro-3-(hexylsulfanyl)pyrazine (III),which is condensed with rac-exo-1-azabicyclo[2.2.1]heptan-3-ol (IV) by means of NaH in THF afforing the target compound as a racemic mixture that is submitted to optical resolution with tartaric acid.The intermediate -exo-1-azabicyclo[2.2.1]heptan-3-ol (IV) has been obtained as follows:The reduction of 1-azabicyclo[2.2.1]heptan-3-one (V) with H2 over PtO2in ethanol gives the corresponding endo-alcohol (VI),which is esterified under Mitsunobu conditions (PPh3,diisopropyl azodicarboxylate (DIAD) and benzoyl chloride) yielding the exo-benzoate (VII).The hydrolysis of (VII) with sodium methoxide in methanol affords the target exo-alcohol (IV).