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【结 构 式】 
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【药物名称】 【化学名称】4-Chloro-N-[4-[1H-imidazol-4(5)-yl]butyl]benzylsulfonamide 【CA登记号】 【 分 子 式 】C14H18ClN3O2S 【 分 子 量 】327.83546 |
【开发单位】James Black Foundation (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Antidepressants, Antiepileptic Drugs, Asthma Therapy, GASTROINTESTINAL DRUGS, Irritable Bowel Syndrome, Agents for, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, RESPIRATORY DRUGS, Sedative/Hypnotics, Sleep Disorders, Treatment of, Histamine H3 Receptor Antagonists |
合成路线1
The known 5-(4-chlorobutyl)-2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl) imidazole (I) was hydrolyzed with HCl in boiling aqueous ethanol and then protected as the triphenylmethyl derivative (II) using trityl chloride and triethylamine. The required primary amine (V) was obtained by condensation of chloride (II) with potassium phthalimide (III), followed by hydrazinolysis of the resulting N-alkylated phthalimide (IV). Sulfonylation of amine (V) with 4-chlorobenzylsulfonyl chloride (VI) gave rise to the sulfonamide (VII). The trityl protecting group of (VII) was finally removed by acid treatment.
| 【1】 Kalindjian, S.B.; Shankley, N.P.; Tozer, M.J.; McDonald, I.M.; Pether, M.J.; Harper, E.A.; Watt, G.F.; Cooke, T.; Low, C.M.R. (James Black Foundation Ltd.); Histamine H3 receptor ligands. EP 0882023; JP 2000505428; US 6080871; WO 9729092 . |
| 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) | 43124 | 2-[tert-butyl(dimethyl)silyl]-5-(4-chlorobutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide | C15H30ClN3O2SSi | 详情 | 详情 | |
| (II) | 43125 | 5-(4-chlorobutyl)-1-trityl-1H-imidazole | C26H25ClN2 | 详情 | 详情 | |
| (III) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
| (IV) | 43126 | 2-[4-(1-trityl-1H-imidazol-5-yl)butyl]-1H-isoindole-1,3(2H)-dione | C34H29N3O2 | 详情 | 详情 | |
| (V) | 43127 | 4-(1-trityl-1H-imidazol-5-yl)-1-butanamine; 4-(1-trityl-1H-imidazol-5-yl)butylamine | C26H27N3 | 详情 | 详情 | |
| (VI) | 43129 | (4-chlorophenyl)methanesulfonyl chloride | 6966-45-6 | C7H6Cl2O2S | 详情 | 详情 |
| (VII) | 43128 | (4-chlorophenyl)-N-[4-(1-trityl-1H-imidazol-5-yl)butyl]methanesulfonamide | C33H32ClN3O2S | 详情 | 详情 |