【结 构 式】 |
【分子编号】44134 【品名】5-chloro-N-(5-chloro-2-pyridinyl)-2-nitrobenzamide 【CA登记号】 |
【 分 子 式 】C12H7Cl2N3O3 【 分 子 量 】312.1114 【元素组成】C 46.18% H 2.26% Cl 22.72% N 13.46% O 15.38% |
合成路线1
该中间体在本合成路线中的序号:(III)The condensation between 5-chloro-2-nitrobenzoyl chloride (I) and 2-amino-5-chloropyridine (II) produced the corresponding amide (III). Subsequent catalytic hydrogenation of the nitro group of (III) gave aniline (IV). Acid chloride (VI), prepared from N-Boc-isonipecotic acid (V) and oxalyl chloride, was then coupled to aniline (IV) to furnish amide (VII). Further trifluoroacetic acid-promoted cleavage of the Boc protecting group of (VII) yielded piperidine (VIII). Finally, reductive alkylation with acetone in the presence of sodium triacetoxyborohydride gave rise to the target N-isopropyl piperidine.
【1】 Kyle, J.A.; et al.; SAR investigations of N-aryl-2-[(piperidin-4-ylcarbonyl)amino]benzamide factor Xa inhibitors. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 288. |
【2】 Aromatic amides. WO 0039118 . |
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) | 44133 | 5-chloro-2-nitrobenzoyl chloride | C7H3Cl2NO3 | 详情 | 详情 | |
(II) | 18559 | 5-Chloro-2-pyridinylamine; 5-Chloro-2-pyridinamine; 2-Amino-5-chloropyridine | 1072-98-6 | C5H5ClN2 | 详情 | 详情 |
(III) | 44134 | 5-chloro-N-(5-chloro-2-pyridinyl)-2-nitrobenzamide | C12H7Cl2N3O3 | 详情 | 详情 | |
(IV) | 44135 | 2-amino-5-chloro-N-(5-chloro-2-pyridinyl)benzamide | C12H9Cl2N3O | 详情 | 详情 | |
(V) | 17404 | 1-(tert-butoxycarbonyl)-4-piperidinecarboxylic acid; 1-BOC-piperidine-4-carboxylic acid; N-Boc-isonipecotic acid | 84358-13-4 | C11H19NO4 | 详情 | 详情 |
(VI) | 44136 | tert-butyl 4-(chlorocarbonyl)-1-piperidinecarboxylate | C11H18ClNO3 | 详情 | 详情 | |
(VII) | 44137 | tert-butyl 4-[(4-chloro-2-[[(5-chloro-2-pyridinyl)amino]carbonyl]anilino)carbonyl]-1-piperidinecarboxylate | C23H26Cl2N4O4 | 详情 | 详情 | |
(VIII) | 44138 | N-(4-chloro-2-[[(5-chloro-2-pyridinyl)amino]carbonyl]phenyl)-4-piperidinecarboxamide | C18H18Cl2N4O2 | 详情 | 详情 |