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【结 构 式】 
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【分子编号】48106 【品名】benzyl 4-(3-[4-[(tert-butoxycarbonyl)amino]-3-pyridinyl]-2-propynyl)-3-oxo-1-piperazinecarboxylate 【CA登记号】 |
【 分 子 式 】C25H28N4O5 【 分 子 量 】464.52128 【元素组成】C 64.64% H 6.08% N 12.06% O 17.22% |
合成路线1
该中间体在本合成路线中的序号：(XII)Iodination of 4-aminopyridine (VI), followed by protection with Boc2O, provided the N-Boc iodopyridine (VIII). Piperazinone (XI) was prepared by alkylation of 4-(benzyloxycarbonyl)-2-piperazinone (IX) with propargyl bromide (X). Palladium-catalyzed coupling of propargyl piperazinone (XI) with iodopyridine (VIII) furnished adduct (XII), which was subsequently cyclized to the pyrrolopyridine derivative (XIII) upon treatment with DBU. The benzyloxycarbonyl group of (XIII) was then cleaved by transfer hydrogenolysis to yield the intermediate piperazinone (XIV).
| 【2】 Myers, M.R.; Becker, M.R.; Ewing, W.R.; Spada, A.P. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. WO 0032590; WO 0107436 . |
| 【1】 Hanney, B.A.; He, W.; Poli, G.B.; Spada, A.P.; Myers, M.R.; Burns, C.J.; Pauls, H.W.; Jiang, J.Z.; Condon, S.M.; Ewing, W.R.; Becker, M.R.; Li, A.; Choi-Sledeski, Y.M.; Lau, W.F.; Davis, R.S. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. EP 1051176; WO 9937304 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 25661 | 4-pyridinamine; 4-aminopyridine | 5044-74-5 | C5H6N2 | 详情 | 详情 |
| (VII) | 48102 | 3-iodo-4-pyridinamine; 3-iodo-4-pyridinylamine | C5H5IN2 | 详情 | 详情 | |
| (VIII) | 48103 | tert-butyl 3-iodo-4-pyridinylcarbamate | C10H13IN2O2 | 详情 | 详情 | |
| (IX) | 48104 | benzyl 3-oxo-1-piperazinecarboxylate | C12H14N2O3 | 详情 | 详情 | |
| (X) | 11176 | 3-Bromopropyne; 3-Bromo-1-propyne | 106-96-7 | C3H3Br | 详情 | 详情 |
| (XI) | 48105 | benzyl 3-oxo-4-(2-propynyl)-1-piperazinecarboxylate | C15H16N2O3 | 详情 | 详情 | |
| (XII) | 48106 | benzyl 4-(3-[4-[(tert-butoxycarbonyl)amino]-3-pyridinyl]-2-propynyl)-3-oxo-1-piperazinecarboxylate | C25H28N4O5 | 详情 | 详情 | |
| (XIII) | 48107 | tert-butyl 2-([4-[(benzyloxy)carbonyl]-2-oxo-1-piperazinyl]methyl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate | C25H28N4O5 | 详情 | 详情 | |
| (XIV) | 48108 | tert-butyl 2-[(2-oxo-1-piperazinyl)methyl]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate | C17H22N4O3 | 详情 | 详情 |