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【结 构 式】 
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【分子编号】56110 【品名】N-methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine; N-methyl(2-methyl-1H-indol-3-yl)methanamine 【CA登记号】 |
【 分 子 式 】C11H14N2 【 分 子 量 】174.24564 【元素组成】C 75.82% H 8.1% N 16.08% |
合成路线1
该中间体在本合成路线中的序号：(II)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).
| 【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：(II)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.
| 【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 |