　 -Drug Synthesis Database

【结构式】

【分子编号】62528

【品名】　

【CA登记号】

【分子式】C₇H₈N₂O₂

【分子量】152.1528

【元素组成】C 55.26% H 5.3% N 18.41% O 21.03%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

6-Quinoxalinecarboxylic acid (III) was prepared by condensation of 3,4-diaminobenzoic acid (I) with glyoxal (II). The title amide was then prepared by coupling of acid (III) with piperidine (VI) via formation of the mixed anhydride (IV) with pivaloyl chloride and Et3N or, alternatively, via activation of (III) as the imidazolide (V) by treatment with carbonyldiimidazole

参考文献中间体

合成目标

【1】 Lynch, G.S.; Rogers, G.A. (University of California, Oakland); Drugs that enhance synaptic responses mediated by AMPA receptors. EP 1156043; JP 1995509468; WO 9402475 .

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)	62528			C₇H₈N₂O₂	详情	详情
(II)	32557	glyoxal; 2-oxoacetaldehyde	107-22-2	C₂H₂O₂	详情	详情
(III)	62529	6-quinoxalinecarboxylic acid		C₉H₆N₂O₂	详情	详情
(IV)	62530	1,1-dimethylpropanoic 6-quinoxalinecarboxylic anhydride		C₁₄H₁₄N₂O₃	详情	详情
(V)	62531	1H-imidazol-1-yl(6-quinoxalinyl)methanone		C₁₂H₈N₄O	详情	详情
(VI)	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The cyclization of 3,4-diaminobenzoic acid (I) with 4-nitrobenzaldehyde (II) in nitrobenzene at 160 C gives 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylic acid (III), which is condensed with 2-aminopyridine (IV) by means of CDI in DMF to yield the corresponding amide (V). The reduction of the nitro group of (V) with H2 over Pd/C in methanol affords 2-(4-aminophenyl)-N-(2-pyridinyl)-1H-benzimidazole-5-carboxamide (VI). Finally, this compound is condensed with adamantane-1-carboxylic acid (VII) to provide the target diamide.

参考文献中间体

合成目标

【1】 Sircar, J.C.; Richards, M.L.; Major, M.W. (Avanir Pharmaceuticals); Benzimidazole cpds. for modulating IgE and inhibiting cellular proliferation. EP 1368028; WO 0272090 .

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)	62528			C₇H₈N₂O₂	详情	详情
(II)	18184	4-Nitrobenzaldehyde	555-16-8	C₇H₅NO₃	详情	详情
(III)	64591	2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylic acid		C₁₄H₉N₃O₄	详情	详情
(IV)	11305	2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine	504-29-0	C₅H₆N₂	详情	详情
(V)	64592	2-(4-nitrophenyl)-N-(2-pyridinyl)-1H-benzimidazole-5-carboxamide		C₁₉H₁₃N₅O₃	详情	详情
(VI)	64593	2-(4-aminophenyl)-N-(2-pyridinyl)-1H-benzimidazole-5-carboxamide		C₁₉H₁₅N₅O	详情	详情
(VII)	64594	tricyclo[3.3.1.1~3,7~]decane-1-carbonyl chloride		C₁₁H₁₅ClO	详情	详情

Extended Information