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【结 构 式】 
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【分子编号】54043 【品名】(1R)-2-{4-[(4-methyl-1-piperazinyl)methyl]-2-nitroanilino}-1-phenyl-1-ethanol 【CA登记号】 |
【 分 子 式 】C20H26N4O3 【 分 子 量 】370.4516 【元素组成】C 64.85% H 7.07% N 15.12% O 12.96% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of 4-fluoro-3-nitrobenzoic acid (I) with 1-methylpiperazine (II) by means of oxalyl chloride in dichloromethane gives the expected acyl derivative (III), which is reduced with BH3/THF to yield the benzyl piperazine (IV). The condensation of (IV) with 2(R)-hydroxy-2-phenylethylamine (V) by means of DIEA in NMP affords the secondary amine (VI), which is reduced with H2 over Pd/C in ethanol, providing the phenylenediamine (VII). Finally, this compound is cyclized with 4-methoxybenzoyl isothiocyanate (VIII) by means of EDC in DMF to furnish the target benzimidazole.
| 【1】 Heyer, D.; et al.; 2-Aminobenzimidazoles: A class of orally bioavailable and brain permeable neuropeptide YY5 antagonists. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 284. |
| 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) | 46937 | 4-fluoro-3-nitrobenzoic acid | 453-71-4 | C7H4FNO4 | 详情 | 详情 |
| (II) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (III) | 54041 | (4-fluoro-3-nitrophenyl)(4-methyl-1-piperazinyl)methanone | C12H14FN3O3 | 详情 | 详情 | |
| (IV) | 54042 | 1-(4-fluoro-3-nitrobenzyl)-4-methylpiperazine | C12H16FN3O2 | 详情 | 详情 | |
| (V) | 10173 | (1R)-2-Amino-1-phenyl-1-ethanol | 2549-14-6 | C8H11NO | 详情 | 详情 |
| (VI) | 54043 | (1R)-2-{4-[(4-methyl-1-piperazinyl)methyl]-2-nitroanilino}-1-phenyl-1-ethanol | C20H26N4O3 | 详情 | 详情 | |
| (VII) | 54044 | (1R)-2-{2-amino-4-[(4-methyl-1-piperazinyl)methyl]anilino}-1-phenyl-1-ethanol | C20H28N4O | 详情 | 详情 | |
| (VIII) | 54045 | 4-Methoxybenzoyl isothiocyanate | 16778-84-0 | C9H7NO2S | 详情 | 详情 |