ethyl 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoate -Drug Synthesis Database

【结构式】

【分子编号】16494

【品名】ethyl 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoate

【CA登记号】

【分子式】C₁₀H₁₂N₄O₃

【分子量】236.23044

【元素组成】C 50.84% H 5.12% N 23.72% O 20.32%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The condensation of adenine (I) with ethyl acrylate (II) by means of NaOEt in refluxing ethanol gives 3-(6-amino-1,6-dihydro-9H-purin-9-yl)propionic acid ethyl ester (III), which is treated with NaNO2 and HOAc to yield 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionic acid ethyl ester (IV). Finally, this compound is treated with 1-(3-aminopropyl)-2-pyrrolidinone (V) in refluxing acetonitrile to afford the target propionamide.

参考文献中间体

合成目标

【1】 Glasky, A.J.; Multi-functional pharmaceutical cpds. and methods of use. WO 9114434 .

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)	10343	9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine	73-24-5	C₅H₅N₅	详情	详情
(II)	10164	ethyl acrylate	140-88-5	C₅H₈O₂	详情	详情
(III)	54214	ethyl 3-(6-amino-1,6-dihydro-9H-purin-9-yl)propanoate	n/a	C₁₀H₁₅N₅O₂	详情	详情
(IV)	16494	ethyl 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoate		C₁₀H₁₂N₄O₃	详情	详情
(V)	52036	N-(3-Aminopropyl)-2-pyrrolidinone; N-(3'-Aminopropyl)-2-pyrrolidinone	7663-77-6	C₇H₁₄N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The condensation of adenine (I) with ethyl acrylate (II) by means of sodium ethoxide in methanol gives 3-(9-adenyl)propionic acid ethyl ester (III), which is treated with NaNO2/acetic acid yielding 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionic acid ethyl ester (IV). The hydrolysis of (IV) with KOH in water affords the corresponding free acid (V), which is esterified with 4-chlorophenyl trifluoroacetate (VI) in pyridine giving the expected 4-chlorophenyl ester (VII). The condensation of ester (VII) with ethyl 4-aminobenzoate (VIII) by heating (35-40 C) in DMSO yields 4-[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionamido]benzoic acid ethyl ester (IX), which is finally hydrolyzed with KOH in water.

参考文献中间体

合成目标

【1】 Graul, A.; Castañer, J.; AIT-082. Drugs Fut 1997, 22, 9, 945.
【2】 Glasky, A.J.; Multi-functional pharmaceutical cpds. and methods of use. WO 9114434 .

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)	10343	9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine	73-24-5	C₅H₅N₅	详情	详情
(II)	10164	ethyl acrylate	140-88-5	C₅H₈O₂	详情	详情
(III)	16493	ethyl 3-(6-amino-9H-purin-9-yl)propanoate		C₁₀H₁₃N₅O₂	详情	详情
(IV)	16494	ethyl 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoate		C₁₀H₁₂N₄O₃	详情	详情
(V)	16495	3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionic acid		C₈H₈N₄O₃	详情	详情
(VI)	16496	4-[(2,2,2-trifluoroacetyl)oxy]benzoic acid		C₉H₅F₃O₄	详情	详情
(VII)	16497	4-[[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoyl]oxy]benzoic acid		C₁₅H₁₂N₄O₅	详情	详情
(VIII)	16498	Benzocaine; ethyl 4-aminobenzoate	94-09-7	C₉H₁₁NO₂	详情	详情
(IX)	16499	ethyl 4-[[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoyl]amino]benzoate		C₁₇H₁₇N₅O₄	详情	详情

Extended Information