3-(2-methoxyphenoxy)-N-(3-pyridinylmethyl)aniline; N-[3-(2-methoxyphenoxy)phenyl]-N-(3-pyridinylmethyl)amine -Drug Synthesis Database

【结构式】

【分子编号】55160

【品名】3-(2-methoxyphenoxy)-N-(3-pyridinylmethyl)aniline; N-[3-(2-methoxyphenoxy)phenyl]-N-(3-pyridinylmethyl)amine

【CA登记号】

【分子式】C₁₉H₁₈N₂O₂

【分子量】306.3642

【元素组成】C 74.49% H 5.92% N 9.14% O 10.44%

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：(VI)

Coupling of 2-methoxyphenol (I) with 3-fluoronitrobenzene (II) produced the diaryl ether (III). The nitro group of (III) was then reduced by catalytic hydrogenation over Raney-Ni, yielding aniline (IV). Reductive alkylation of (IV) with pyridine-3-carboxaldehyde (V) using NaBH4 furnished the secondary amine (VI). This was finally acylated with 2,2,2-trifluoroethylsulfonyl chloride to produce the title sufonamide.

参考文献中间体

合成目标

【1】 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)	13182	Guaiacol; 2-Methoxyphenol	90-05-1	C₇H₈O₂	详情	详情
(II)	55157	1-Fluoro-3-nitrobenzene; 3-Fluoro-1-nitrobenzene; 3-Fluoronitrobenzene; 3-Nitrofluorobenzene; m-Fluoronitrobenzene	402-67-5	C₆H₄FNO₂	详情	详情
(III)	55158	2-methoxyphenyl 3-nitrophenyl ether; 1-methoxy-2-(3-nitrophenoxy)benzene		C₁₃H₁₁NO₄	详情	详情
(IV)	55159	3-(2-methoxyphenoxy)phenylamine; 3-(2-methoxyphenoxy)aniline		C₁₃H₁₃NO₂	详情	详情
(V)	12849	Nicotinaldehyde; 3-Pyridinecarboxaldehyde	500-22-1	C₆H₅NO	详情	详情
(VI)	55160	3-(2-methoxyphenoxy)-N-(3-pyridinylmethyl)aniline; N-[3-(2-methoxyphenoxy)phenyl]-N-(3-pyridinylmethyl)amine		C₁₉H₁₈N₂O₂	详情	详情

Extended Information