N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]acrylamide -Drug Synthesis Database

【结构式】

【分子编号】56111

【品名】N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]acrylamide

【CA登记号】

【分子式】C₁₄H₁₆N₂O

【分子量】228.29392

【元素组成】C 73.66% H 7.06% N 12.27% O 7.01%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

2-Methyl-3-(methylaminomethyl)indole (II) was obtained by the reductive amination of indole aldehyde (I) with methylamine. Acylation of amine (II) with acryloyl chloride (III) furnished the corresponding acrylamide (IV).

参考文献中间体

合成目标

【1】 Uzinskas, I.N.; Miller, W.H.; Newlander, K.A.; Jakas, D.R.; Seefeld, M.A.; DeWolf, W.E. Jr. (GlaxoSmithKline Inc.); Fab I inhibitors. EP 1226138; WO 0127103 .

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)	56109	2-Meethylindole-3-carboxaldehyde		C₁₀H₉NO	详情	详情
(II)	56110	N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine; N-methyl(2-methyl-1H-indol-3-yl)methanamine		C₁₁H₁₄N₂	详情	详情
(III)	11577	Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride	814-68-6	C₃H₃ClO	详情	详情
(IV)	56111	N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]acrylamide		C₁₄H₁₆N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The title compound was obtained from the bromo naphthyridinone (X) by two related methods. Palladium-catalyzed Heck coupling of bromide (X) with acrylamide (IV) yielded directly the desired naphthyridinyl acrylamide. Alternatively, bromo naphthyridinone (X) was subjected to Heck coupling with tert-butyl acrylate (XI) to give adduct (XII). After acidic cleavage of the tert-butyl ester group of (XII), the resultant naphthyridinyl acrylic acid (XIII) was coupled to the indolylmethyl amine (II) to furnish the desired amide.

参考文献中间体

合成目标

【1】 Seefeled, M.A.; et al.; Discovery and characterization of highly potent naphthyridine-based FabI inhibitors with in vivo activity. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-1690.
【2】 Uzinskas, I.N.; Miller, W.H.; Newlander, K.A.; Jakas, D.R.; Seefeld, M.A.; DeWolf, W.E. Jr. (GlaxoSmithKline Inc.); Fab I inhibitors. EP 1226138; WO 0127103 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	56110	N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine; N-methyl(2-methyl-1H-indol-3-yl)methanamine		C₁₁H₁₄N₂	详情	详情
(IV)	56111	N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]acrylamide		C₁₄H₁₆N₂O	详情	详情
(X)	56116	6-bromo-3,4-dihydro[1,8]naphthyridin-2(1H)-one		C₈H₇BrN₂O	详情	详情
(XI)	12760	tert-butyl acrylate	1663-39-4	C₇H₁₂O₂	详情	详情
(XII)	56117	tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro[1,8]naphthyridin-3-yl)-2-propenoate		C₁₅H₁₈N₂O₃	详情	详情
(XIII)	56118	(E)-3-(7-oxo-5,6,7,8-tetrahydro[1,8]naphthyridin-3-yl)-2-propenoic acid		C₁₁H₁₀N₂O₃	详情	详情

Extended Information