【结 构 式】 |
【药物名称】 【化学名称】6-Amino-2-butyl-9-(4-fluorobenzyl)-9H-purin-8-ol 【CA登记号】228107-55-9 【 分 子 式 】C16H18FN5O 【 分 子 量 】315.35316 |
【开发单位】Japan Energy (Originator), Sumitomo Pharmaceuticals (Originator) 【药理作用】Anti-Hepatitis C Virus Drugs, Anti-Hepatitis Virus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs, Interferon Inducers |
合成路线1
Condensation of 4-amino-5-cyanoimidazole (I) with pentanamide (II) upon heating at 210 C produced the 2-butyladenine (III). Subsequent alkylation of (III) with 4-fluorobenzyl chloride (IV) yielded the 9-fluorobenzyl adenine (V). This was brominated at position 8 using Br2 and NaOAc in HOAc. The resultant 8-bromo adenine (VI) was finally hydrolyzed under acidic conditions to the title 8-hydroxy derivative.
【1】 Matsui, H.; Takaku, H.; Isobe, Y.; Ogita, H.; Tobe, M.; Tomizawa, H. (Japan Energy Corp.); Type 2 helper T cell-selective immune response suppressors. EP 1043021; US 6376501; WO 9932122 . |
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) | 52898 | 4(5)-Amino-1H-imidazole-5(4)-carbonitrile; 4(5)-Amino-5(4)-cyanoimidazole | 5098-11-3 | C4H4N4 | 详情 | 详情 |
(II) | 52899 | Pentanamide; Valeramide; n-Valeramide | 626-97-1 | C5H11NO | 详情 | 详情 |
(III) | 52900 | 2-butyl-9H-purin-6-amine; 2-butyl-9H-purin-6-ylamine | C9H13N5 | 详情 | 详情 | |
(IV) | 12354 | 4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene | 352-11-4 | C7H6ClF | 详情 | 详情 |
(V) | 52901 | 2-butyl-9-(4-fluorobenzyl)-9H-purin-6-amine; 2-butyl-9-(4-fluorobenzyl)-9H-purin-6-ylamine | C16H18FN5 | 详情 | 详情 | |
(VI) | 52902 | 8-bromo-2-butyl-9-(4-fluorobenzyl)-9H-purin-6-ylamine; 8-bromo-2-butyl-9-(4-fluorobenzyl)-9H-purin-6-amine | C16H17BrFN5 | 详情 | 详情 |
Extended Information