|
【结 构 式】 
|
【分子编号】61732 【品名】4-amino-N-(5-{[(5-{[(2-{[amino(imino)methyl]amino}ethyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide 【CA登记号】 |
【 分 子 式 】C21H28N10O3 【 分 子 量 】468.51892 【元素组成】C 53.84% H 6.02% N 29.9% O 10.24% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The reaction of ethylenediamine (I) with Boc2O in dioxane gives the monocarbamate (II), which is condensed with O-methylisourea (III) to yield the aminoguanidine carbamate (IV). The cleavage of the carbamate group of (IV) by means of HCl in methanol affords the aminoguanidine (V), which is condensed with 1-methyl-4-nitropyrrole-2-carbonyl chloride (VI) by means of NaHCO3 in dioxane/water to provide the amide (VII). The reduction of the nitro group of (VII) by means of H2 over Pd/C in 1N HCl affords the 4-aminopyrrole-2-carboxamide (VIII), which is condensed with the acid chloride (VI) as before to give the diamide (IX). Reduction of the nitro group of (IX) under the same conditions described above yields the amino diamide (X), which is condensed with the 14-labeled acid chloride (XI) as described above to afford the triamide (XII). Further reduction of the nitro group of (XII) gives the amino triamide (XIII), which is finally condensed with 4-(2-bromopropenamido)-1-methylpyrrole-2-carbonyl chloride (XIV) by means of NaHCO3 in dioxane/water to yield the target 14C labeled pentaamide compound.
| 【1】 Fontana, E.; Pignatti, A.; Synthesis of brostallicin (PNU-166196A) labelled with 2H and 14C. Label. Cop. & Radiopharm. 2002, 45, 11, 899. |
| 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) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
| (II) | 13241 | N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate；tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate | 57260-73-8 | C7H16N2O2 | 详情 | 详情 |
| (III) | 26657 | O-methyl isourea; [Amino(imino)methoxy]methane | 52328-05-9 | C2H6N2O | 详情 | 详情 |
| (IV) | 41436 | tert-butyl 2-[[amino(imino)methyl]amino]ethylcarbamate | C8H18N4O2 | 详情 | 详情 | |
| (V) | 41437 | N-(2-aminoethyl)guanidine | C3H10N4 | 详情 | 详情 | |
| (VI) | 27852 | 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride | C6H5ClN2O3 | 详情 | 详情 | |
| (VII) | 41445 | N-(2-[[amino(imino)methyl]amino]ethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide | C9H14N6O3 | 详情 | 详情 | |
| (VIII) | 41446 | 4-amino-N-(2-[[amino(imino)methyl]amino]ethyl)-1-methyl-1H-pyrrole-2-carboxamide | C9H16N6O | 详情 | 详情 | |
| (IX) | 41447 | N-(2-[[amino(imino)methyl]amino]ethyl)-1-methyl-4-[[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino]-1H-pyrrole-2-carboxamide | C15H20N8O4 | 详情 | 详情 | |
| (X) | 41448 | N-(2-[[amino(imino)methyl]amino]ethyl)-4-[[(4-amino-1-methyl-1H-pyrrol-2-yl)carbonyl]amino]-1-methyl-1H-pyrrole-2-carboxamide | C15H22N8O2 | 详情 | 详情 | |
| (XI) | 65171 | 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride | 28494-51-1 | C6H5ClN2O3 | 详情 | 详情 |
| (XII) | 41443 | N-(2-[[amino(imino)methyl]amino]ethyl)-1-methyl-4-[[(1-methyl-4-[[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino]-1H-pyrrol-2-yl)carbonyl]amino]-1H-pyrrole-2-carboxamide | C21H26N10O5 | 详情 | 详情 | |
| (XIII) | 61732 | 4-amino-N-(5-{[(5-{[(2-{[amino(imino)methyl]amino}ethyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide | C21H28N10O3 | 详情 | 详情 | |
| (XIV) | 41441 | 4-[(2-bromoacryloyl)amino]-1-methyl-1H-pyrrole-2-carbonyl chloride | C9H8BrClN2O2 | 详情 | 详情 |