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【结 构 式】

【分子编号】44135

【品名】2-amino-5-chloro-N-(5-chloro-2-pyridinyl)benzamide

【CA登记号】

【 分 子 式 】C12H9Cl2N3O

【 分 子 量 】282.12848

【元素组成】C 51.09% H 3.22% Cl 25.13% N 14.89% O 5.67%

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:(IV)

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

合成路线2

该中间体在本合成路线中的序号:(XIII)

An alternative preparation for the title compound consisted in the reductive alkylation of ethyl isonipecotate (IX) with acetone to afford the N-isopropyl isonipecotate (X). After basic hydrolysis of the ethyl ester group of (X), the resulting carboxylic acid (XI) was activated as the mixed anhydride (XII) with isobutyl chloroformate. Anhydride (XII) was finally coupled to aniline (IV) to generate the required amide.

1 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
(IX) 17410 Ethyl isonipecotate; ethyl 4-piperidinecarboxylate 1126-09-6 C8H15NO2 详情 详情
(X) 44139 ethyl 1-isopropyl-4-piperidinecarboxylate C11H21NO2 详情 详情
(XI) 44140 1-isopropyl-4-piperidinecarboxylic acid C9H17NO2 详情 详情
(XII) 44141   C14H25NO4 详情 详情
(XIII) 44135 2-amino-5-chloro-N-(5-chloro-2-pyridinyl)benzamide C12H9Cl2N3O 详情 详情
Extended Information