Methanol → 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid methyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	Methanol	HCID 887	—
反応物	3,5-Dichlorosalicylaldehyde	HCID 66660	—
反応物	Sodium triacetoxyborohydride	HCID 5049666	—
反応物	2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester	HCID 69067985	—
溶媒	Dimethylsulfoxide acetic acid	HCID 18355466	—
生成物	2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid methyl ester	HCID 10195352	—

反応条件

温度	50 °C

反応手順

After dissolving 2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester (20 mg, 0.055 mmol) in dimethylsulfoxide-acetic acid (10:1), 2-hydroxy-3,5-dichlorobenzaldehyde (32.0 mg, 0.166 mmol) and sodium triacetoxyborohydride (35.0 mg, 0.166 mg) were added and the mixture was stirred at 50° C. for 2 days. Methanol (1 ml) was added to the reaction mixture, and then after stirring for 1 minute, it was purified by SCX solid phase extraction (Bond Elute SCX500MG). The product was further purified by preparative HPLC to obtain 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid methyl ester. The compound was identified by LC-MS.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07517875B2
出典データセット	uspto-grants-2009_04
ORD ID	ord-432aaa06404b40bea99d45bff01826f0
出典メモ	uspto-grants-2009_04