N,N-dimethyl-N-[4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolyl]amine; N,N-dimethyl-4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine -Drug Synthesis Database

【结构式】

【分子编号】18586

【品名】N,N-dimethyl-N-[4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolyl]amine; N,N-dimethyl-4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine

【CA登记号】

【分子式】C₁₁H₁₇N₃O

【分子量】207.2756

【元素组成】C 63.74% H 8.27% N 20.27% O 7.72%

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：(VIII)

Condensation of 3-pyridylacetonitrile (I) with dimethyl-formamide dimethylacetal (II) afforded dimethylaminomethylene compound (III), which was cyclized to isoxazole (IV) by treatment with hydroxylamine.HCl in AcOH at 100 C. Quaternization with iodomethane provided pyridinium salt (V), and subsequent reduction with NaBH4 in MeOH produced tetrahydropyridine (VI). Then, methylation with iodomethane in the presence of KOH gave a mixture of monomethylated (VII) and dimethylated (VIII) compounds, which were separated by column chromatography. Finally, the major methylamino compound (VII) was converted to the oxalate salt.

参考文献中间体

合成目标

【1】 Olesen, P.H.; Swedberg, M.D.B.; Rimvall, K.; 3-(5-Alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridines: A novel class of central nicotinic receptor ligands. Bioorg Med Chem 1998, 6, 9, 1623.

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)	18579	2-(3-pyridinyl)acetonitrile	6443-85-2	C₇H₆N₂	详情	详情
(II)	11984	N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal	4637-24-5	C₅H₁₃NO₂	详情	详情
(III)	18581	(Z)-3-(dimethylamino)-2-(3-pyridinyl)-2-propenenitrile		C₁₀H₁₁N₃	详情	详情
(IV)	18582	4-(3-pyridinyl)-5-isoxazolamine; 4-(3-pyridinyl)-5-isoxazolylamine		C₈H₇N₃O	详情	详情
(V)	18583	3-(5-amino-4-isoxazolyl)-1-methylpyridinium iodide		C₉H₁₀IN₃O	详情	详情
(VI)	18584	4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine; 4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolylamine		C₉H₁₃N₃O	详情	详情
(VII)	18585	N-methyl-N-[4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolyl]amine; N-methyl-4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine		C₁₀H₁₅N₃O	详情	详情
(VIII)	18586	N,N-dimethyl-N-[4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolyl]amine; N,N-dimethyl-4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine		C₁₁H₁₇N₃O	详情	详情

Extended Information