Bucindolol hydrochloride, MJ-13105-1

9-(2-氯-6-氟苯甲基)-N-甲基-9H-嘌呤-6-胺 布新洛尔 Chemical Name: 2-[2-Hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile monohydrochloride; o-[2-Hydroxy-3-[(2-indol-3-yl-1,1-dimethylethyl)amino]propoxy]benzonitrile monohydrochloride
CAS No. 70369-47-0, 71119-11-4 (free base)
项目整合开发状态: Discontinued
项目研究机构: Bristol-Myers Squibb (Originator), Aeolus Pharmaceuticals (Licensee), ARCA (Licensee)
合成路线:By reaction of 3-(2-methyl-2-aminopropyl)indole (I) and 2-(2,3-epoxypropoxy)benzonitrile (II) by heating at 120-40 C followed by a treatment with HCl in ethanol.The starting products are obtained as follows:1) The reaction of 3-(dimethylaminomethyl)indole (III) with 2-nitropropane (IV) by means of KOH gives 3-(2-methyl-2-nitropropyl)indole (V),which is then reduced with hydrazine and Raney-Ni in ethanol to yield (I).2) The reaction of 2-hydroxybenzonitrile (VI) with epichlorohydrin (VII) by means of piperidine affords 2-(3-chloro-2-hydroxypropoxy)benzonitrile (VIII),which is epoxidized again to (II) by treatment with NaOH in hot THF-water.