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【结 构 式】 
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【分子编号】63252 【品名】2-[(tert-butylamino)sulfonyl]-5-isobutyl-3-thienylboronic acid 【CA登记号】 |
【 分 子 式 】C12H22BNO4S2 【 分 子 量 】319.25402 【元素组成】C 45.15% H 6.95% B 3.39% N 4.39% O 20.05% S 20.09% |
合成路线1
该中间体在本合成路线中的序号：(IV)4-Chloro-5-formyl-2-phenylimidazole (I) is alkylated with 4-bromobenzyl bromide (II) in the presence of K2CO3 in DMF to produce the N-bromobenzyl imidazole (III). Subsequent Suzuki coupling between aryl bromide (III) and 5-isobutyl-2-[(N-tert-butyl)sulfonamido]thiophene-3-boronic acid (IV) affords the thienylphenyl derivative (V). The N-tert-butyl group is then removed by treatment with trifluoroacetic acid in the presence of anisole, yielding sulfonamide (VI). Displacement of the chloro substituent of (VI) with MeOH/NaOH furnishes the 4-methoxy imidazole (VII). Finally, condensation of sulfonamide (VII) with ethyl isocyanate gives rise to the target N-sulfonyl urea compound.
| 【1】 Wiemer, G.; Heitsch, H. (Aventis Pharma Deutschland GmbH); 1-(p-Thienylbenzyl)-imidazoles as angiotensin-(1-7) receptor agonists, method for the production and the utilization thereof and pharmaceutical preparations containing said cpds.. EP 1185527; JP 2002544130; US 6235766; US 6429222; WO 0068226 . |
| 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) | 63250 | 4-chloro-2-phenyl-1H-imidazole-5-carbaldehyde | C10H7ClN2O | 详情 | 详情 | |
| (II) | 16109 | 1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide | 589-15-1 | C7H6Br2 | 详情 | 详情 |
| (III) | 63251 | 1-(4-bromobenzyl)-4-chloro-2-phenyl-1H-imidazole-5-carbaldehyde | C17H12BrClN2O | 详情 | 详情 | |
| (IV) | 63252 | 2-[(tert-butylamino)sulfonyl]-5-isobutyl-3-thienylboronic acid | C12H22BNO4S2 | 详情 | 详情 | |
| (V) | 63253 | N-(tert-butyl)-3-{4-[(4-chloro-5-formyl-2-phenyl-1H-imidazol-1-yl)methyl]phenyl}-5-isobutyl-2-thiophenesulfonamide | C29H32ClN3O3S2 | 详情 | 详情 | |
| (VI) | 63254 | 3-{4-[(4-chloro-5-formyl-2-phenyl-1H-imidazol-1-yl)methyl]phenyl}-5-isobutyl-2-thiophenesulfonamide | C25H24ClN3O3S2 | 详情 | 详情 | |
| (VII) | 63255 | 3-{4-[(5-formyl-4-methoxy-2-phenyl-1H-imidazol-1-yl)methyl]phenyl}-5-isobutyl-2-thiophenesulfonamide | C26H27N3O4S2 | 详情 | 详情 |