【结 构 式】 |
【分子编号】62344 【品名】methyl 4-fluoro-3-(trifluoromethyl)benzoate 【CA登记号】 |
【 分 子 式 】C9H6F4O2 【 分 子 量 】222.1390528 【元素组成】C 48.66% H 2.72% F 34.21% O 14.4% |
合成路线1
该中间体在本合成路线中的序号:(II)4-Fluoro-3-trifluoromethylbenzoic acid (I) is esterified employing MeOH and SOCl2 to afford the methyl ester (II). Displacement of the 4-fluoride of (II) with N-benzylpiperazine (III) in hot DMSO yields the piperazinyl benzoate (IV). The N-benzyl group of (IV) is then removed by hydrogenolysis over Pd/C to yield the deprotected piperazine (V), which is further coupled with 2-pyrrolecarboxylic acid (VI) by means of CDI producing amide (VII). Finally, displacement of the methyl ester of (VII) with guanidine (VIII) gives rise to the target acyl guanidine, which is converted to the corresponding mesylate salt
【1】 Roos, O.; Eickmeier, C.; Blech, S.-M.; Búrger, E. (Boehringer Ingelheim Pharma GmbH & Co. KG); Benzoylguanidine derivs. with advantageous properties, method for producing them and their use in the production of medicaments. DE 19843489; JP 2002538077; US 6323207; WO 0017176 . |
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) | 62343 | 4-fluoro-3-(trifluoromethyl)benzoic acid | C8H4F4O2 | 详情 | 详情 | |
(II) | 62344 | methyl 4-fluoro-3-(trifluoromethyl)benzoate | C9H6F4O2 | 详情 | 详情 | |
(III) | 28542 | N-Benzylpiperazine; 1-Benzylpiperazine | 2759-28-6 | C11H16N2 | 详情 | 详情 |
(IV) | 62345 | methyl 4-(4-benzyl-1-piperazinyl)-3-(trifluoromethyl)benzoate | C20H21F3N2O2 | 详情 | 详情 | |
(V) | 62346 | methyl 4-(1-piperazinyl)-3-(trifluoromethyl)benzoate | C13H15F3N2O2 | 详情 | 详情 | |
(VI) | 31796 | Pyrrole-2-carboxylic acid; 1H-pyrrole-2-carboxylic acid | 634-97-9 | C5H5NO2 | 详情 | 详情 |
(VII) | 62347 | methyl 4-[4-(1H-pyrrol-2-ylcarbonyl)-1-piperazinyl]-3-(trifluoromethyl)benzoate | C18H18F3N3O3 | 详情 | 详情 | |
(VIII) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |