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【结 构 式】

【药物名称】MBT

【化学名称】2-(5-tert-Butyl-1H-indol-3-yl)-N-methyl-1-ethanamine

【CA登记号】

【 分 子 式 】C15H22N2

【 分 子 量 】230.35599

【开发单位】Lilly (Originator), Synaptic (Originator)

【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Antimigraine Drugs, 5-HT1D Agonists

合成路线1

Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl, followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II). Fisher indolization with 4-chlorobutyraldehyde (IV), (obtained by hydrogenation of acid chloride (III)), then afforded tryptamine (V). In an alternative procedure, 4-phthalimidobutyraldehyde diethyl acetal (VIII) was prepared by treatment of amine (VI) with N-carbethoxyphthalimide (VII). Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (IX), which was deprotected with hydrazine to furnish the corresponding tryptamine (V). Subsequent condensation of (V) with di-tert-butyl dicarbonate gave carbamate (X). This was finally reduced by means of LiAlH4 providing the target N-methyl tryptamine.

1 Xu, Y.-C.; Schaus, J.M.; Walker, C.; Krushinski, J.; Adhamm, N.; Zgombick, J.M.; Liang, S.X.; Kohlman, D.T.; Audia, J.E.; N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist. J Med Chem 1999, 42, 3, 526.
2 Audia, J.E.; Cohen, M.L.; Gidda, J.S.; Nelson, D.L.G.; Baker, S.R.; Ezquerra-Carrera, J.; Lamas-Peteira, C.; Pedregal-Tercero, C. (Eli Lilly and Company); Method for treating 5HT2B receptor related conditions. EP 0749313; JP 1997510216; US 5663178; WO 9524200; WO 9624351 .
3 Audia, J.E.; et al. (Eli Lilly and Company); Intermediates to tetrahydro-beta-carbolines. US 5635528 .
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) 27492 4-(tert-butyl)aniline 769-92-6 C10H15N 详情 详情
(II) 29269 1-[4-(tert-butyl)phenyl]hydrazine C10H16N2 详情 详情
(III) 11265 4-Chlorobutanoyl chloride; 4-Chlorobutyric acid chloride 4635-59-0 C4H6Cl2O 详情 详情
(IV) 23428 4-Chlorobutanal C4H7ClO 详情 详情
(V) 29270 2-[5-(tert-butyl)-1H-indol-3-yl]-1-ethanamine C14H20N2 详情 详情
(VI) 23323 4,4-diethoxybutylamine; 4,4-diethoxy-1-butanamine 6346-09-4 C8H19NO2 详情 详情
(VII) 10283 ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide 22509-74-6 C11H9NO4 详情 详情
(VIII) 23325 2-(4,4-diethoxybutyl)-1H-isoindole-1,3(2H)-dione C16H21NO4 详情 详情
(IX) 29271 2-[2-[5-(tert-butyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione C22H22N2O2 详情 详情
(X) 29272 tert-butyl 2-[5-(tert-butyl)-1H-indol-3-yl]ethylcarbamate C19H28N2O2 详情 详情
Extended Information