Norzimelidine, Botiacrine, CPP-199, A-24356, -Drug Synthesis Database

【结构式】

【药物名称】Norzimelidine, Botiacrine, CPP-199, A-24356

【化学名称】N-[3-(4-Bromophenyl)-3-(3-pyridinyl)-2(Z)-propenyl]-N-methylamine

【CA登记号】60324-59-6

【分子式】C₁₅H₁₅BrN₂

【分子量】303.2042

【开发单位】

【药理作用】　

合成路线1 合成路线2

合成路线1

The condensation of 4-bromophenyl-3-pyridyl ketone (I) with ethyl bromoacetate (II) by means of Zn in refluxing benzene gives ethyl 3-hydroxy-3-(3-pyridyl)-3-(4-bromophenyl)propionate (III), which is reduced with LiAlH4 in refluxing ethyl ether yielding 1-(3-pyridyl)-1-(4-bromophenyl)propane-1,3-diol (IV). Finally this compound is treated first with PBr3 and HBr in refluxing acetone, and then with methylamine (V) at 110 C in a pressure vessel

参考文献中间体

【1】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Sweetman, A.J.; Nomelidine. Drugs Fut 1979, 4, 12, 885.
【2】 Carlsson, P.A.E.; et al. (Astra Lakemedel AB); BE 835802; DD 122528; DE 2550005; FR 2291751; JP 7676278; NL 7513648; ZA 7506893 .

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)	60939	(4-bromophenyl)(3-pyridinyl)methanone		C₁₂H₈BrNO	详情	详情
(II)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(III)	60940	ethyl 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridinyl)propanoate		C₁₆H₁₆BrNO₃	详情	详情
(IV)	60941	1-(4-bromophenyl)-1-(3-pyridinyl)-1,3-propanediol		C₁₄H₁₄BrNO₂	详情	详情
(V)	11021	Methanamine; Methylamine	74-89-5	CH₅N	详情	详情

合成路线2

The condensation of 4-bromophenyl-3-pyridyl ketone (I) with ethyl bromoacetate (II) by means of Zn in refluxing benzene gives ethyl 3-hydroxy-3-(3-pyridyl)-3-(4-bromophenyl)propionate (III), which is converted into the corresponding methylamide (VI) by treatment with methylamine (V) in ethanol. This compound is reduced with NaBH4 in THF yielding 3-(3-pyridyl)-3-(4-bromophenyl)-3-hydroxy-N-methylpropylamine (VII), which is finally dehydrated by treatment with 50% H2SO4 at 110 C

参考文献中间体

【1】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Sweetman, A.J.; Nomelidine. Drugs Fut 1979, 4, 12, 885.
【2】 Carlsson, P.A.E.; et al. (Astra Lakemedel AB); BE 835802; DD 122528; DE 2550005; FR 2291751; JP 7676278; NL 7513648; ZA 7506893 .

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)	60939	(4-bromophenyl)(3-pyridinyl)methanone		C₁₂H₈BrNO	详情	详情
(II)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(III)	60940	ethyl 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridinyl)propanoate		C₁₆H₁₆BrNO₃	详情	详情
(V)	11021	Methanamine; Methylamine	74-89-5	CH₅N	详情	详情
(VI)	60942	3-(4-bromophenyl)-3-hydroxy-N-methyl-3-(3-pyridinyl)propanamide		C₁₅H₁₅BrN₂O₂	详情	详情
(VII)	60943	1-(4-bromophenyl)-3-(methylamino)-1-(3-pyridinyl)-1-propanol		C₁₅H₁₇BrN₂O	详情	详情

Extended Information