【结 构 式】 |
【分子编号】32797 【品名】6-(5-chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl vinyl carbonate 【CA登记号】 |
【 分 子 式 】C14H9ClN4O4 【 分 子 量 】332.70272 【元素组成】C 50.54% H 2.73% Cl 10.66% N 16.84% O 19.24% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号:(S)-(III)The esterification of (rac)-6-(5-chloro-3-pyridyl)-5-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-7-one rac-(I) with vinyl chloroformate (II) in pyridine gives the racemic carbonate rac-(III), which is submitted to an enantioselective hydrolysis with Candida antarctica (SP 435L) lipase in dioxane/benzyl alcohol yielding a mixture of rac-(I), which is recycled, and enantiomerically pure (95% e.e.) (S)-(III). Finally, this compound is condensed with 1-methylpiperazine (IV) in acetone.
【1】 Culy, C.; Castañer, J.; Bayes, M.; Eszopiclone. Drugs Fut 2003, 28, 7, 640. |
【2】 Cotrel, C.; Roussel, G. (Aventis Pharma SA); Optically active deriv. of 5H-pyrrolo[3,4-b]pyrazine, its preparation and pharmaceutical compsns. containing it. EP 0495717; EP 0609210; FR 2671800; JP 1994504548; WO 9212980 . |
【3】 Gotor, V.; et al.; Enzymic resolution of (±)-6-(5-chloropyridin-2-yl)-7-vinyloxycarbonyloxy-6,7-dihydro[5H] pyrrolo[3,4-b]pyrazin-5-one. Synthesis of (+)-zopiclone. Tetrahedron Asymmetry 1997, 8, 7, 995. |
【4】 Bayod Jasanada, M.S.; Brieva Collado, R.; Linares López, F.J.; García Campos, R.; Gotor Santamaría, V. (Asturpharma SA); (+)-6-(5-Chloropyrid-2-yl)-7-oxo-vinylcarbonyloxy-5,6-dihydropyrrolo[3,4b]pyrazine and their use in a process for the preparation of (+)-6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)-carbonyloxy-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine. ES 2101653 . |
【5】 Cotrel, C.; et al. (Aventis Pharma SA); Pyrrolo-[3,4,b]pyrazine derivatives. DE 2300491; GB 1358680; JP 52048687; US 3862149 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
rac-(I) | 32796 | 6-(5-chloro-2-pyridinyl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one | C11H7ClN4O2 | 详情 | 详情 | |
(S)-(III) | 32797 | 6-(5-chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl vinyl carbonate | C14H9ClN4O4 | 详情 | 详情 | |
rac-(III) | 32798 | (5S)-6-(5-chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl vinyl carbonate | C14H9ClN4O4 | 详情 | 详情 | |
(II) | 28068 | 1-[(Chlorocarbonyl)oxy]ethylene; Vinyl chloroformate | 5130-24-5 | C3H3ClO2 | 详情 | 详情 |
(IV) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
Extended Information