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【结 构 式】 
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【药物名称】BM-519 【化学名称】N2-Cyano-N1-[2-(3-methylphenylamino)-5-nitrophenylsulfonyl]azepine-1-carboxamidine 【CA登记号】 【 分 子 式 】C21H24N6O4S 【 分 子 量 】456.52723 |
【开发单位】University of Namur (Originator) 【药理作用】Antiplatelet Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Prostanoid TP (Thromboxane A2) Antagonists |
合成路线1
The reaction of 2-chloro-5-nitroaniline (I) with NaNO2 in HCl and HOAc, followed by addition of CuCl2 and SO2 yields sulfonyl chloride (II). Reaction of (II) with NH4OH affords sulfonamide (III), which is then treated 3-methylaniline (IV) in 3-chlorotoluene to furnish intermediate (V). Final conversion of (V) into the target product is achieved by treatment in H2O/acetone with NaOH and carbamimidothioate (VIII), which can be obtained by reaction of dimethyl N-cyanodithioiminocarbonate (VI) with amine (VII) in EtOH.
| 【1】 Delarge, J.; Masereel, B.; Dogne, J.-M. (University of Liege); Benzenic sulphonamide derivs. and their uses. WO 0042004 . |
| 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) | 43033 | 2-chloro-5-nitroaniline; 2-chloro-5-nitrophenylamine | 6283-25-6 | C6H5ClN2O2 | 详情 | 详情 |
| (II) | 43034 | 2-chloro-5-nitrobenzenesulfonyl chloride;2-Chloro-5-nitro-benzenesulfonyl chloride;2-Chloro-5-nitrophenylsulfonyl chloride;6-Chloro-3-nitrobenzenesulfonyl chloride | 4533-95-3 | C6H3Cl2NO4S | 详情 | 详情 |
| (III) | 43035 | 2-chloro-5-nitrobenzenesulfonamide | 96-72-0 | C6H5ClN2O4S | 详情 | 详情 |
| (IV) | 30687 | 3-methylphenylamine; m-toluidine | 108-44-1 | C7H9N | 详情 | 详情 |
| (V) | 43036 | 5-nitro-2-(3-toluidino)benzenesulfonamide | C13H13N3O4S | 详情 | 详情 | |
| (VI) | 43037 | [[bis(methylsulfanyl)methylene]amino]methane | C4H9NS2 | 详情 | 详情 | |
| (VII) | 18672 | azepane | 111-49-9 | C6H13N | 详情 | 详情 |
| (VIII) | 43038 | methyl N-cyano-1-azepanecarbimidothioate | C9H15N3S | 详情 | 详情 |