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【结 构 式】 
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【药物名称】PHD-321 【化学名称】N-[1-Benzyl-2-[1-(1-naphthyl)ethylamino]ethyl]-3,4-dimethoxybenzenesulfonamide hydrochloride 【CA登记号】 【 分 子 式 】C29H33ClN2O4S 【 分 子 量 】541.11436 |
【开发单位】CNRS (Originator) 【药理作用】ENDOCRINE DRUGS, Thyroid Disease Therapy |
合成路线1
The condensation of allyl benzene (II) with (4-nitrophenylsulfonylimino)phenyliodinane (I) by means of Cu-OTf or Cu(OTf)2 in acetonitrile gives the sulfonyl aziridine (III), which is treated with 1-(1-naphthyl)ethylamine (IV) to yield the sulfonamide (V). The cleavage of the 4-nitrophenylsulfonyl group of (V) by means of thiophenol, DMSO and K2CO3 in hot acetonitrile affords the primary amine (VI), which is finally condensed with 3,4-dimetoxyphenylsulfonyl chloride (VII) and TEA in dichloromethane to provide the target sulfonamide.
| 【1】 Dauban, P.; et al.; N1-Arylsulfonyl-N2-(1-aryl)ethyl-3-phenylpropane-1,2-diamines as novel calcimimetics acting on the calcium sensing receptor. Bioorg Med Chem Lett 2000, 10, 17, 2001. |
| 【2】 Potier, P.J.-P.S.J.; Ruat, M.; Dauban, P.M.; Faure, H.V.; Dodd, R. (CNRS (Centre National de la Recherche Scientifique)); Aralkyl-1,2-diamines having calcimimetic activity and preparation mode. WO 0134562 . |
| 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) | 47464 | 4-nitro-N-[(E)-phenyl-lambda(3)-iodanylidene]benzenesulfonamide | C12H9IN2O4S | 详情 | 详情 | |
| (II) | 47465 | 1-allylbenzene | 300-57-2 | C9H10 | 详情 | 详情 |
| (III) | 47466 | 2-benzyl-1-[(4-nitrophenyl)sulfonyl]aziridine | C15H14N2O4S | 详情 | 详情 | |
| (IV) | 47470 | 1-(1-naphthyl)ethylamine; 1-(1-naphthyl)-1-ethanamine | C12H13N | 详情 | 详情 | |
| (V) | 47467 | N-(1-benzyl-2-[[1-(1-naphthyl)ethyl]amino]ethyl)-4-nitrobenzenesulfonamide | C27H27N3O4S | 详情 | 详情 | |
| (VI) | 47468 | N-(2-amino-3-phenylpropyl)-N-[1-(1-naphthyl)ethyl]amine; N(1)-[1-(1-naphthyl)ethyl]-3-phenyl-1,2-propanediamine | C21H24N2 | 详情 | 详情 | |
| (VII) | 47469 | 3,4-dimethoxybenzenesulfonyl chloride | 23095-31-0 | C8H9ClO4S | 详情 | 详情 |