N-(5-chloro-2-pyridinyl)-3-methoxy-2-nitrobenzamide -Drug Synthesis Database

【结构式】

【分子编号】51186

【品名】N-(5-chloro-2-pyridinyl)-3-methoxy-2-nitrobenzamide

【CA登记号】

【分子式】C₁₃H₁₀ClN₃O₄

【分子量】307.69292

【元素组成】C 50.75% H 3.28% Cl 11.52% N 13.66% O 20.8%

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：(IV)

Treatment of 3-methoxy-2-nitrobenzoic acid (I) with oxalyl chloride gave the corresponding acid chloride (II), which was then coupled with 2-amino-5-chloropyridine (III) to yield amide (IV). The reduction of the nitro group of (IV) using sodium hydrosulfite afforded aniline (V). Further chlorination of (V) with N-chlorosuccinimide furnished the 5-chloro derivative (VI).

参考文献中间体

合成目标

【1】 Cheeseman, S.; Chou, Y.-L.; Ye, B.; et al.; Design, synthesis, and biological activity of novel non-amidine factor Xa inhibitors, 4: Optimization of hydrophilic substituents for potency and oral availability. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 128.
【2】 Snider, R.M.; Liang, A.M.; Wu, S.C.; Arnaiz, D.O.; Sacchi, K.L.; Kochanny, M.J.; Phillips, G.B.; Ye, B.; Zhao, Z.; Morrissey, M.M.; Griedel, B.D.; Lee, W.; Sakata, S.T.; Karanjawala, R.E.; Chou, Y.-L.; Shaw, K.J. (Schering AG); Ortho-anthranilamide derivs. as anticoagulants. EP 1040108; JP 2001526283; US 6140351; WO 9932477 .

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)	25827	3-methoxy-2-nitrobenzoic acid	4920-80-3	C₈H₇NO₅	详情	详情
(II)	25828	3-methoxy-2-nitrobenzoyl chloride		C₈H₆ClNO₄	详情	详情
(III)	18559	5-Chloro-2-pyridinylamine; 5-Chloro-2-pyridinamine; 2-Amino-5-chloropyridine	1072-98-6	C₅H₅ClN₂	详情	详情
(IV)	51186	N-(5-chloro-2-pyridinyl)-3-methoxy-2-nitrobenzamide		C₁₃H₁₀ClN₃O₄	详情	详情
(V)	51187	2-amino-N-(5-chloro-2-pyridinyl)-3-methoxybenzamide		C₁₃H₁₂ClN₃O₂	详情	详情
(VI)	51188			C₁₃H₁₁Cl₂N₃O₂	详情	详情

Extended Information