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【结 构 式】 
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【药物名称】 【化学名称】2-[1-(1-Naphthylsulfonyl)-1H-indol-6-yl]octahydropyrrolo[1,2-a]pyrazine 【CA登记号】 【 分 子 式 】C25H25N3O2S 【 分 子 量 】431.5609 |
【开发单位】NPS Allelix (Originator) 【药理作用】Antidepressants, Antipsychotic Drugs, Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, Cognition Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, 5-HT6 Antagonists |
合成路线1
The reaction of 6-bromo-1H-indole (I) with Tips-Cl and NaH in DMF gives the N-silylated indole (II), which is condensed with 1,4-diazabicyclo[4,3,0]nonane (III) by means of tBu-ONa, Pd(OAc)2 and tBu3P in hot xylene to yield the corresponding adduct (IV). The desilylation of (IV) by means of TBAF in THF affords the deprotected indole (V), which is finally sulfonated with 1-naphthylsulfonyl chloride and NaHMDS in THF.
| 【1】 Isaac, M.; et al.; 6-Bicyclopiperazinyl-1-araylsulfonylindoles and 6-bicyclopiperidinyl-1-arylsulfonylindoles derivatives as novel, potent, and selective 5-HT6 receptor antagonists. Bioorg Med Chem Lett 2000, 10, 15, 1719. |
| 【2】 Isaac, M.; Slassi, A.; Xin, T. (NPS Allelix Corp.); Cpds. having 5-HT6 receptor antagonist activity. WO 0132660 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 30014 | 6-Bromoindole; 6-Bromo-1H-indole | 52415-29-9 | C8H6BrN | 详情 | 详情 |
| (II) | 47471 | 6-bromo-1-(triisopropylsilyl)-1H-indole | C17H26BrNSi | 详情 | 详情 | |
| (III) | 40336 | octahydropyrrolo[1,2-a]pyrazine | C7H14N2 | 详情 | 详情 | |
| (IV) | 47472 | 2-[1-(triisopropylsilyl)-1H-indol-6-yl]octahydropyrrolo[1,2-a]pyrazine | C24H39N3Si | 详情 | 详情 | |
| (V) | 47473 | 2-(1H-indol-6-yl)octahydropyrrolo[1,2-a]pyrazine | C15H19N3 | 详情 | 详情 | |
| (VI) | 18650 | 1-naphthalenesulfonyl chloride | 85-46-1 | C10H7ClO2S | 详情 | 详情 |