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【结 构 式】 
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【分子编号】50161 【品名】4-(acetamido)-N-[5-(hydroxymethyl)-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-imidazole-2-carboxamide 【CA登记号】 |
【 分 子 式 】C13H17N5O3 【 分 子 量 】291.30988 【元素组成】C 53.6% H 5.88% N 24.04% O 16.48% |
合成路线1
该中间体在本合成路线中的序号：(II)The pyrrolecarboxylic acid derivative (I) was treated with BOP reagent, and the resulting hydroxybenzotriazolyl ester was reduced in situ with NaBH4 to furnish alcohol (II). Oxidation of (II) by means of activated MnO2 produced aldehyde (III). Wadsworth-Emmons reaction of aldehyde (III) with triethylphosphonoacetate gave rise to the unsaturated ester (IV). After basic hydrolysis of the ester group of (IV), the resultant carboxylic acid (V) was activated as the imidazolide (VI) upon treatment with carbonyldiimidazole. This was finally coupled with the segment A of DU86 (VII) in the presence of NaH in DMF at low temperature to yield the target amide.
| 【1】 Tao, Z.-F.; et al.; Highly cooperative DNA dialkylation by the homodimer of imidazole - Pyrrole diamide - CPI conjugate with vinyl linker. J Am Chem Soc 2000, 122, 8, 1602. |
| 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) | 50160 | 4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrole-2-carboxylic acid | C13H15N5O4 | 详情 | 详情 | |
| (II) | 50161 | 4-(acetamido)-N-[5-(hydroxymethyl)-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-imidazole-2-carboxamide | C13H17N5O3 | 详情 | 详情 | |
| (III) | 50162 | 4-(acetamido)-N-(5-formyl-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-imidazole-2-carboxamide | C13H15N5O3 | 详情 | 详情 | |
| (IV) | 50163 | ethyl (E)-3-[4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrol-2-yl]-2-propenoate | C17H21N5O4 | 详情 | 详情 | |
| (V) | 50164 | (E)-3-[4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrol-2-yl]-2-propenoic acid | C15H17N5O4 | 详情 | 详情 | |
| (VI) | 50165 | 4-(acetamido)-N-[5-[(E)-3-(1H-imidazol-1-yl)-3-oxo-1-propenyl]-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-imidazole-2-carboxamide | C18H19N7O3 | 详情 | 详情 | |
| (VII) | 38365 | methyl (3bR,4aS)-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate | C14H14N2O3 | 详情 | 详情 |