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【结 构 式】

【分子编号】53901

【品名】6-[(dimethylamino)methyl]-3-[2-iodo(methyl)anilino]-2-cyclohexen-1-one

【CA登记号】n/a

【 分 子 式 】C16H21IN2O

【 分 子 量 】384.26009

【元素组成】C 50.01% H 5.51% I 33.03% N 7.29% O 4.16%

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)

Condensation of 2-iodoaniline (I) with cyclohexane-1,3-dione (II) at 120 C yields secondary amine (III), which is then methylated with iodomethane by means of sodium hydride in refluxing benzene to provide tertiary amine (IV). Treatment of (IV) with lithium diisopropylamide (LDA) and dimethylaminomethylene iodide (Eschenmoser's salt) (V) in THF yields dimethylaminomethyl derivative (VI), which is then coupled with 2-methylindole (VII) in DMF to give compound (VIII). Cyclization of cyclohexenone derivative (VIII) by means of palladium (II) acetate and triethylamine in acetonitrile provides carbazolone derivative (IX), which is finally converted into the desired hydrochloride salt by treatment with HCl.

1 Bell, J.A.; Ewan, G.B.; Humber, D.C.; Costes, I.H.; Godfrey, N. (GlaxoSmithKline plc); Process for the preparation of 3-imidazolylmethyltetrahydrocarbazolones. EP 0221629 .
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) 27725 2-iodoaniline 615-43-0 C6H6IN 详情 详情
(II) 11244 1,3-Cyclohexanedione 504-02-9 C6H8O2 详情 详情
(III) 53899 3-(2-iodoanilino)-2-cyclohexen-1-one n/a C12H12INO 详情 详情
(IV) 53900 3-[2-iodo(methyl)anilino]-2-cyclohexen-1-one n/a C13H14INO 详情 详情
(V) 48555 Eschenmoser's salt; N,N-Dimethylmethyleneimmonium chloride; N,N-Dimethylmethyleneimmonium iodide C3H8IN 详情 详情
(VI) 53901 6-[(dimethylamino)methyl]-3-[2-iodo(methyl)anilino]-2-cyclohexen-1-one n/a C16H21IN2O 详情 详情
(VII) 15670 2-Methylimidazole; 2-Methyl-1H-imidazole 693-98-1 C4H6N2 详情 详情
(VIII) 53902 3-[2-iodo(methyl)anilino]-6-[(2-methyl-1H-imidazol-1-yl)methyl]-2-cyclohexen-1-one n/a C18H20IN3O 详情 详情
(IX) 53903 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one n/a C18H19N3O 详情 详情
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