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【结 构 式】 
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【药物名称】PNU-177864 【化学名称】N-[4-[2-(Propylamino)ethyl]phenyl]-4-(trifluoromethoxy)benzenesulfonamide 【CA登记号】250266-51-4 【 分 子 式 】C18H21F3N2O3S 【 分 子 量 】402.43887 |
【开发单位】Pfizer (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, Dopamine D3 Antagonists |
合成路线1
4-Nitrophenethylamine (I) was acylated with propionyl chloride and the resulting amide (II) was reduced to amine (III) with borane-dimethyl sulfide complex in refluxing THF. Amine (III) was then protected as the tert-butyl carbamate (IV) using Boc2O in THF. Subsequent catalytic hydrogenation of the nitro group of (IV) over Pd/C furnished aniline (V), which was coupled with 4-(trifluoromethoxy)benzenesulfonyl chloride (VI) to yield sulfonamide (VII). The Boc protecting group of (VII) was finally removed by treatment with trifluoroacetic acid.
| 【1】 Romero, A.G.; Leiby, J.A. (Pharmacia Corp.); Phenylsulfonamide-phenylethylamines useful as dopamine receptors. EP 1077935; WO 9958499 . |
| 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) | 26560 | 4-nitrophenethylamine | 24954-67-4 | C8H10N2O2 | 详情 | 详情 |
| (II) | 47983 | N-(4-nitrophenethyl)propanamide | C11H14N2O3 | 详情 | 详情 | |
| (III) | 47984 | N-(4-nitrophenethyl)-1-propanamine; N-(4-nitrophenethyl)-N-propylamine | C11H16N2O2 | 详情 | 详情 | |
| (IV) | 47985 | tert-butyl 4-nitrophenethyl(propyl)carbamate | C16H24N2O4 | 详情 | 详情 | |
| (V) | 47986 | tert-butyl 4-aminophenethyl(propyl)carbamate | C16H26N2O2 | 详情 | 详情 | |
| (VI) | 47987 | 4-(trifluoromethoxy)benzenesulfonyl chloride | 94108-56-2 | C7H4ClF3O3S | 详情 | 详情 |
| (VII) | 47988 | tert-butyl propyl[4-([[4-(trifluoromethoxy)phenyl]sulfonyl]amino)phenethyl]carbamate | C23H29F3N2O5S | 详情 | 详情 |