4-{[2-(methyloxy)phenyl]oxy}aniline; 4-{[2-(methyloxy)phenyl]oxy}phenylamine -Drug Synthesis Database

【结构式】

【分子编号】65013

【品名】4-{[2-(methyloxy)phenyl]oxy}aniline; 4-{[2-(methyloxy)phenyl]oxy}phenylamine

【CA登记号】

【分子式】C₁₃H₁₃NO₂

【分子量】215.25176

【元素组成】C 72.54% H 6.09% N 6.51% O 14.87%

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：(I)

The reductive alkylation of 4-(2-methoxyphenoxy)aniline (I) with pyridine-3-carboxaldehyde (II) in the presence of NaBH4 leads to the N-pyridylmethyl aniline adduct (III) (1). Alternatively, 4-bromoaniline (IV) is reductively alkylated with pyridine-3-carboxaldehyde (II) to produce (V). Subsequent copper-catalyzed bromide displacement of (V) with guaiacol (VI) affords intermediate (III) (2). Finally, acylation of amine (III) with 2,2,2-trifluoroethylsulfonyl chloride (VII) gives rise to the target sulfonamide (1,2).

参考文献中间体

合成目标

【1】 Johnson, M.P.; Baez, M.; Jagdmann, G.E.Jr.; Britton, T.C.; Large, T.H.; Callagaro, D.O.; Tizzano, J.P.; Monn, J.A.; Schoepp, D.D.; Discovery of allosteric potentiators for the metabotropic glutamate 2 receptor: Synthesis and subtype selectivity of N-(4-(2-methoxyphenoxy)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine. J Med Chem 2003, 46, 15, 3189.
【2】 Monn, J.A.; Hornback, W.J.; Schoepp, D.D.; Dressman, B.A.; Britton, T.C.; Tizzano, J.P.; Johnson, K.W.; Henry, S.S.; Coleman, D.S.; Jagdmann, G.E.J.; Johnson, M.P.; Large, T.H.; Barda, D.A.; Fichtner, M.W. (Eli Lilly and Company); Potentiators of glutamate receptors. WO 0156990 .

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)	65013	4-{[2-(methyloxy)phenyl]oxy}aniline; 4-{[2-(methyloxy)phenyl]oxy}phenylamine		C₁₃H₁₃NO₂	详情	详情
(II)	12849	Nicotinaldehyde; 3-Pyridinecarboxaldehyde	500-22-1	C₆H₅NO	详情	详情
(III)	65014	N-(4-{[2-(methyloxy)phenyl]oxy}phenyl)-N-(3-pyridinylmethyl)amine; 4-{[2-(methyloxy)phenyl]oxy}-N-(3-pyridinylmethyl)aniline		C₁₉H₁₈N₂O₂	详情	详情
(IV)	22531	4-Bromoaniline; 4-Bromophenylamine	106-40-1	C₆H₆BrN	详情	详情
(V)	65015	4-bromo-N-(3-pyridinylmethyl)aniline; N-(4-bromophenyl)-N-(3-pyridinylmethyl)amine		C₁₂H₁₁BrN₂	详情	详情
(VI)	13052	4-((5R,5aR,8aR,9S)-9-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxyphenyl dibenzyl phosphate		C₄₃H₄₅O₁₆P	详情	详情
(VII)	65016	2,2,2-trifluoro-1-ethanesulfonyl chloride		C₂H₂ClF₃O₂S	详情	详情

Extended Information