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【结 构 式】 
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【分子编号】61766 【品名】[(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5-{[6-(diethylamino)-1-benzofuran-2-yl]carbonyl}-1H-indol-2-yl)methanone 【CA登记号】 |
【 分 子 式 】C34H31ClN4O4 【 分 子 量 】595.0974 【元素组成】C 68.62% H 5.25% Cl 5.96% N 9.41% O 10.75% |
合成路线1
该中间体在本合成路线中的序号：(X)The reaction of indoline (I) with propynoic acid methyl ester (II) in methanol gives the acrylic acid derivative (III), which is cyclized by means of Pd(OAc)2 in DMA to yield the pyrroloindole (IV). The reduction of the ester group of (IV) by means of BH3/Me2S in refluxing THF affords intermediate (V), which is treated with CCl4 and PPh3 to provide the chloromethyl derivative (VI). The O-deprotection in (VI) by means of HCOONH4 and Pd/C in THF gives the hydroxy compound (VII), which is N-deprotected by means of HCl in ethyl acetate to yield the pyrroloindole (VIII). The condensation of (VIII) with the known indole carboxylic acid (IX) by means of EDC in DMF affords the carboxamide (X), which is treated with phenyl isocyanate (XI) and TEA in THF to provide the target Carzelesin.
| 【1】 Fukuda, Y.; et al.; Novel syntheses of optically active CC-1065, U-73,975 (adozelesin), U-80,244 (carzelesin), U-77,779 (bizelesin), KW-2189, and DU-86. Heterocycles 1997, 45, 12, 2303. |
| 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) | 59123 | tert-butyl (3S)-3-[(acetyloxy)methyl]-5-amino-6-(benzyloxy)-2,3-dihydro-1H-indole-1-carboxylate | C23H28N2O5 | 详情 | 详情 | |
| (II) | 19588 | methyl propiolate | 922-67-8 | C4H4O2 | 详情 | 详情 |
| (III) | 59124 | tert-butyl (3S)-3-[(acetyloxy)methyl]-6-(benzyloxy)-5-{[(E)-3-methoxy-3-oxo-1-propenyl]amino}-2,3-dihydro-1H-indole-1-carboxylate | C27H32N2O7 | 详情 | 详情 | |
| (IV) | 59126 | 6-(tert-butyl) 1-methyl (8S)-8-[(acetyloxy)methyl]-4-(benzyloxy)-7,8-dihydropyrrolo[3,2-e]indole-1,6(3H)-dicarboxylate | C27H30N2O7 | 详情 | 详情 | |
| (V) | 59127 | tert-butyl (1S)-5-(benzyloxy)-1-(hydroxymethyl)-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate | C24H28N2O4 | 详情 | 详情 | |
| (VI) | 59128 | tert-butyl (1S)-5-(benzyloxy)-1-(chloromethyl)-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate | C24H27ClN2O3 | 详情 | 详情 | |
| (VII) | 59129 | tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate | C17H21ClN2O3 | 详情 | 详情 | |
| (VIII) | 59130 | (8S)-8-(chloromethyl)-1-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indol-4-ol | C12H13ClN2O | 详情 | 详情 | |
| (IX) | 61765 | 5-{[6-(diethylamino)-1-benzofuran-2-yl]carbonyl}-1H-indole-2-carboxylic acid | C22H20N2O4 | 详情 | 详情 | |
| (X) | 61766 | [(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5-{[6-(diethylamino)-1-benzofuran-2-yl]carbonyl}-1H-indol-2-yl)methanone | C34H31ClN4O4 | 详情 | 详情 | |
| (XI) | 11289 | 1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate | 103-71-9 | C7H5NO | 详情 | 详情 |