Diisopropylethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxamide

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylethylamine	HCID 81531	—
反応物	5-Chloro-1H-indole-3-ethylamine monohydrochloride	HCID 2827494	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
反応物	Ethyl 5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxylate	HCID 66832124	—
溶媒	Methanol	HCID 887	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Sodium Hydroxide	HCID 14798	—
生成物	N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxamide	HCID 49869045	36.1%

反応手順

This compound was prepared according to method F with ethyl 5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxylate (0.126 g; 0.433 mmol) in methanol (1 mL) and sodium hydroxide in water (2M, 1 mL); and 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.433 mmol), HATU (0.164 g; 0.432 mmol), N,N diisopropylethylamine (0.075 mL; 0.432 mmol), in DMF (4 mL). The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.069 g (36%) of the N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxamide as a white solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09434722B2
出典データセット	uspto-grants-2016_09
ORD ID	ord-d9bc744e71ab4a8783cc1d0bc926dda0
出典メモ	uspto-grants-2016_09