SK&F-94120, -Drug Synthesis Database

【结构式】

【药物名称】SK&F-94120

【化学名称】5-(4-Acetamidophenyl)pyrazin-2(1H)-one

【CA登记号】89541-55-9

【分子式】C₁₂H₁₁N₃O₂

【分子量】229.24037

【开发单位】GlaxoSmithKline (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, Hypertension, Treatment of, Vasodilators, Phosphodiesterase III Inhibitors

合成路线1 合成路线2

合成路线1

1) By condensation of 2 chloropyrazine (I) with N-acetylphenylhydroxylamine (II) by means of NaH in DMF (or NaOH in DMF - water; or with K2CO3 in acetone).

参考文献中间体

【1】 Coates, W.J. (SmithKline Beecham plc); 5-(4-Nitrophenyl)-2(1H)-pyrazinones. EP 0096517; US 4514568; US 4556711 .
【2】 Prous, J.; Castaner, J.; SK&F-94120. Drugs Fut 1986, 11, 2, 129.

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)	24075	2-chloropyrazine	14508-49-7	C₄H₃ClN₂	详情	详情
(II)	24080	N-hydroxy-N-phenylacetamide		C₈H₉NO₂	详情	详情

合成路线2

2) The condensation of (I) with benzyl-N-hydroxy-N-phenylcarbamate (III) in ethanolic KOH gives 5-[4-(benzyloxycarbonylamino)phenyl]pyrazin-2(1H)-one (IV), which is hydrolyzed witn HBr in acetic acid yielding 5-(4-aminophenyl)pyrazin-2(1H)-one (V). Finally, this compound is acetylated with acetic anhydride.

参考文献中间体

【1】 Coates, W.J. (SmithKline Beecham plc); 5-(4-Nitrophenyl)-2(1H)-pyrazinones. EP 0096517; US 4514568; US 4556711 .
【2】 Prous, J.; Castaner, J.; SK&F-94120. Drugs Fut 1986, 11, 2, 129.

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)	24075	2-chloropyrazine	14508-49-7	C₄H₃ClN₂	详情	详情
(III)	24076	heptyl hydroxy(phenyl)carbamate		C₁₄H₂₁NO₃	详情	详情
(IV)	24077	heptyl 4-(5-oxo-4,5-dihydro-2-pyrazinyl)phenylcarbamate		C₁₈H₂₃N₃O₃	详情	详情
(V)	24078	4-(4,5-dihydro-2-pyrazinyl)aniline		C₁₀H₁₁N₃	详情	详情

Extended Information