2-(butylamino)-N-(4-methoxy-2-nitrophenyl)-2-oxoacetamide -Drug Synthesis Database

【结构式】

【分子编号】60886

【品名】2-(butylamino)-N-(4-methoxy-2-nitrophenyl)-2-oxoacetamide

【CA登记号】

【分子式】C₁₃H₁₇N₃O₅

【分子量】295.2952

【元素组成】C 52.88% H 5.8% N 14.23% O 27.09%

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：(II)

Treatment of the N-aryl oxalamic acid ethyl ester (I) with butylamine in toluene provides the oxalic diamide (II). The nitro group of (II) is then reduced to the corresponding amine (III) by catalytic hydrogenation over Pd/C. Subsequent thermal cyclization of the N-acyl phenylenediamine (III) leads to benzimidazole (IV). Hydrolysis of both the methyl ether and amide functions of (IV) with concentrated HBr furnishes 6-hydroxy-1H-benzimidazole-2-carboxylic acid (V). Then, coupling of acid (V) with 4-benzylpiperidine (VI) in the presence of TBTU gives rise to the desired amide

参考文献中间体

合成目标

【1】 Nagy, J.; Domany, G.; Farkas, S.; Borza, I.; Horvath, C.; Bartane Szalai, G.; Kolok, S. (Gedeon Richter Ltd.); Amine derivs. as NMDA receptor antagonists. WO 0234718 .

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)	60885	ethyl 2-(4-methoxy-2-nitroanilino)-2-oxoacetate		C₁₁H₁₂N₂O₆	详情	详情
(II)	60886	2-(butylamino)-N-(4-methoxy-2-nitrophenyl)-2-oxoacetamide		C₁₃H₁₇N₃O₅	详情	详情
(III)	60893	N-(2-amino-4-methoxyphenyl)-2-(butylamino)-2-oxoacetamide		C₁₃H₁₉N₃O₃	详情	详情
(IV)	60894	N-butyl-6-methoxy-1H-benzimidazole-2-carboxamide		C₁₃H₁₇N₃O₂	详情	详情
(V)	60985	6-[4-(3-hydroxybutyl)-1-piperazinyl]-N-(6-methoxy-8-quinolinyl)hexanamide		C₂₄H₃₆N₄O₃	详情	详情
(VI)	26225	4-benzylpiperidine	31252-42-3	C₁₂H₁₇N	详情	详情

Extended Information