(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 -Drug Synthesis Database

【结构式】

【分子编号】38965

【品名】(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

【CA登记号】

【分子式】C₂₇H₂₆ClN₅O₅

【分子量】535.98684

【元素组成】C 60.5% H 4.89% Cl 6.61% N 13.07% O 14.93%

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：(XIII)

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.

参考文献中间体

合成目标

【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