tert-butyl 4-(chlorocarbonyl)-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】44136

【品名】tert-butyl 4-(chlorocarbonyl)-1-piperidinecarboxylate

【CA登记号】

【分子式】C₁₁H₁₈ClNO₃

【分子量】247.72156

【元素组成】C 53.33% H 7.32% Cl 14.31% N 5.65% O 19.38%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

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.

参考文献中间体

合成目标

【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

Extended Information