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【结 构 式】

【分子编号】38968

【品名】(3aR,4S,6R,6aR)-6-(6-[(2,2-diphenylethyl)amino]-2-[[2-(1H-imidazol-4-yl)ethyl]amino]-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

【CA登记号】

【 分 子 式 】C34H39N9O4

【 分 子 量 】637.74192

【元素组成】C 64.03% H 6.16% N 19.77% O 10.04%

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:(XVI)

Protection of the 2',3'-diol group of adenosine (VII) as the corresponding acetonide (XII) was effected by treatment with 2,2-dimethoxypropane and p-toluenesulfonic acid. The primary alcohol group of (XII) was then oxidized to carboxylic acid (XIII) using KMnO4. After conversion of (XIII) to acid chloride by means of refluxing SOCl2, coupling with ethylamine furnished amide (XIV). Displacement of the 2-chloro of (XIV) by histamine (XV) in hot DMSO produced adduct (XVI). The acetonide group of (XVI) was finally deprotected using aqueous trifluoroacetic acid.

1 Gregson, M.; Ayres, B.E.; Ewan, G.B.; Ellis, F.; Knight, J. (Glaxo Wellcome plc); 2,6-Diaminopurine derivs.. EP 0680488; JP 1996505864; US 5925624; WO 9417090 .
2 Keeling, S.E.; et al.; The discovery and synthesis of highly potent, A2A receptor agonists. Bioorg Med Chem Lett 2000, 10, 4, 403.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 38961 (2R,3R,4S,5R)-2-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydro-3,4-furandiol C24H24ClN5O4 详情 详情
(XII) 38964 ((3aR,4R,6R,6aR)-6-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol C27H28ClN5O4 详情 详情
(XIII) 38965 (3aR,4S,6R,6aR)-6-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid C27H26ClN5O5 详情 详情
(XIV) 38966 (3aR,4S,6R,6aR)-6-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide C29H31ClN6O4 详情 详情
(XV) 38967 2-(1H-imidazol-4-yl)ethylamine; 2-(1H-imidazol-4-yl)-1-ethanamine 51-45-6 C5H9N3 详情 详情
(XVI) 38968 (3aR,4S,6R,6aR)-6-(6-[(2,2-diphenylethyl)amino]-2-[[2-(1H-imidazol-4-yl)ethyl]amino]-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide C34H39N9O4 详情 详情
Extended Information