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【结 构 式】

【药物名称】

【化学名称】1-[4-[4-[1(S)-[4-(1,3-Benzodioxol-5-ylmethyl)phenyl]ethyl]-3(S)-methylpiperazin-1-yl]piperidin-1-yl]-1-(2,6-dimethylphenyl)methanone

【CA登记号】

【 分 子 式 】C35H43N3O3

【 分 子 量 】553.75126

【开发单位】Schering-Plough (Originator)

【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Chemokine CCR5 Antagonists

合成路线1

The lithium derivative (II), prepared from p-bromo-alpha-methylbenzylamine (I), was added to piperonal (III) to obtain the diaryl carbinol (IV), which was further deoxygenated to (V) using triethylsilane and trifluoroacetic acid. Basic hydrolysis of the trifluoroacetamide function of (V) provided amine (VI). This was then alkylated with the chiral triflate (VII) to afford amino ester (VIII). Subsequent acylation of amine (VIII) with chloroacetyl chloride (IX), followed by cyclization of the resulting chloroacetamide (X) with ammonia, led to the diketopiperazine (XI). Reduction of the carbonyl groups of (XI), followed by reductive amination of the resulting piperazine (XII) with N-Boc-4-piperidinone (XIII), gave the piperidinyl piperazine (XIV). After acidic Boc group cleavage of (XIV), the resulting piperidine (XV) was finally condensed with 2,6-dimethylbenzoic acid (XVI) to yield the target benzamide.

1 Tagat, J.R.; et al.; Piperazine-based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element. Bioorg Med Chem Lett 2001, 11, 16, 2143.
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) 50550 N-[(1S)-1-(4-bromophenyl)ethyl]-2,2,2-trifluoroacetamide C10H9BrF3NO 详情 详情
(II) 50551   C10H8F3Li2NO 详情 详情
(III) 10127 1,3-Benzodioxole-5-carbaldehyde; Heliotropine 120-57-0 C8H6O3 详情 详情
(IV) 50552 N-((1S)-1-[4-[1,3-benzodioxol-5-yl(hydroxy)methyl]phenyl]ethyl)-2,2,2-trifluoroacetamide C18H16F3NO4 详情 详情
(V) 50553 N-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-2,2,2-trifluoroacetamide C18H16F3NO3 详情 详情
(VI) 50554 (1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]-1-ethanamine; (1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethylamine C16H17NO2 详情 详情
(VII) 50555 ethyl (2R)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate C6H9F3O5S 详情 详情
(VIII) 50556 ethyl (2S)-2-([(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]amino)propanoate C21H25NO4 详情 详情
(IX) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(X) 50557 ethyl (2S)-2-[[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl](2-chloroacetyl)amino]propanoate C23H26ClNO5 详情 详情
(XI) 50558 (6S)-1-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-6-methyl-2,5-piperazinedione C21H22N2O4 详情 详情
(XII) 50559 (2S)-1-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-2-methylpiperazine C21H26N2O2 详情 详情
(XIII) 18620 tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone 79099-07-3 C10H17NO3 详情 详情
(XIV) 50560 tert-butyl 4-((3S)-4-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-3-methylpiperazinyl)-1-piperidinecarboxylate C31H43N3O4 详情 详情
(XV) 50561 (2S)-1-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-2-methyl-4-(4-piperidinyl)piperazine C26H35N3O2 详情 详情
(XVI) 50562 m-Xylylic acid; 2,6-Dimethylbenzoic acid; m-Xylene-2-carboxylic acid 632-46-2 C9H10O2 详情 详情
Extended Information