(3aR,4S,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】61425

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

【CA登记号】

【分子式】C₁₅H₁₈ClN₅O₄

【分子量】367.79192

【元素组成】C 48.99% H 4.93% Cl 9.64% N 19.04% O 17.4%

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：(III)

The title compound is prepared by two methods. Chlorination of 2',3'-O-isopropylideneinosine-5'-uronic acid (I) with SOCl2 in the presence of DMF produces the chloropurine acid chloride (II), which is further converted into the amide (III) upon treatment with ethylamine. Subsequent displacement of the purine 6-chloro group of (III) with cyclopentylamine (IV) furnishes the cyclopentylamino purine (V). Finally, acidic ketal hydrolysis in (IV) gives rise to the target compound.

参考文献中间体

合成目标

【1】 Olsson, R.A.; Thompson, R.D. (UCB Pharma, Inc.); N-6 Substd.-5'-(N-substd. carboxamido)adenosines as cardiac vasodilators and antihypertensive agents. AU 8544972; EP 0191025; ES 8609359; JP 1986286398; US 5310731; WO 8600310 .

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)	61423	(3aR,4S,6R,6aR)-2,2-dimethyl-6-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid		C₁₃H₁₄N₄O₆	详情	详情
(II)	61424	(3aR,4S,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl chloride		C₁₃H₁₂Cl₂N₄O₄	详情	详情
(III)	61425	(3aR,4S,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide		C₁₅H₁₈ClN₅O₄	详情	详情
(IV)	28850	cyclopentanamine	1003-03-8	C₅H₁₁N	详情	详情
(V)	61426	(3aR,4S,6R,6aR)-6-[6-(cyclopentylamino)-9H-purin-9-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide		C₂₀H₂₈N₆O₄	详情	详情

Extended Information