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【结 构 式】

【分子编号】28174

【品名】2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline

【CA登记号】

【 分 子 式 】C14H20Br2N2

【 分 子 量 】376.13428

【元素组成】C 44.71% H 5.36% Br 42.49% N 7.45%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The acylation of 2,4-dibromo-6-(N-cyclohexyl-N-methylaminomethyl)aniline (I) with 4-(ethoxycarbonyloxy)-3-methoxybenzoyl chloride (II) in CHCl3 gives the corresponding amide (III), which is deprotected by a treatment with aqueous 20% NaOH.

1 Koshinaka, E.; Ogawa, N.; Kurata, S.; Yamagashi, K.; Kato, I. (Hokuriku Seiyaku Co., Ltd.); 2-Benzoylamino substituted benzylamine derivative and a process for preparation thereof. DE 3209970; EP 0061157; ES 510608 .
2 Chu, S.S.; BR-227. Drugs Fut 1985, 10, 3, 186.
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) 28174 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline C14H20Br2N2 详情 详情
(II) 29039 4-(chlorocarbonyl)-2-methoxyphenyl ethyl carbonate C11H11ClO5 详情 详情
(III) 29040 4-[(2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]anilino)carbonyl]-2-methoxyphenyl ethyl carbonate C25H30Br2N2O5 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

The reaction of cysteine (I) with benzyl chloroformate (II) in the usual way gives the corresponding di(benzyloxycarbonyl) derivative (III), which is treated with PCl5 or SOCl2 in CHCl3 to afford the bisacyl chloride (IV). Finally, this compound is condensed with 4,6-dibromo-2-(cyclohexylmethylaminomethyl) aniline (V) in ethyl acetate.

1 Giannini, E.H.; Farm Sci Ed 1985, 40, 2, 108-119.
2 Nardi, D.; Tajana, A.; Motta, G.; Cazzulani, P.; Graziani, G. (Recordati Industria Chimica e Farmaceutica SpA); Therapeutically effective derivatives of cystine. DE 3225274; EP 0069527; FR 2509298; GB 2102792; JP 58032860; US 4438133 .
3 Castaner, J.; Serradell, M.N.; Cistinexine. Drugs Fut 1986, 11, 3, 181.
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) 28171 (2S)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propionic acid 56-89-3 C6H12N2O4S2 详情 详情
(II) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(III) 28172 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[((2R)-2-[[(benzyloxy)carbonyl]amino]-2-carboxyethyl)disulfanyl]propionic acid 6968-11-2 C22H24N2O8S2 详情 详情
(IV) 27173 (1R)-1-ethyl-2,2-dimethyl-3-butenyl 2-bromoacetate C10H17BrO2 详情 详情
(V) 28174 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline C14H20Br2N2 详情 详情
Extended Information