Diisopropylethylamine → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-isoxazol-3-yl-ethyl)-amide

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylethylamine	HCID 81531	—
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	1-(1,2-Oxazol-3-yl)ethan-1-amine hydrochloride	HCID 55253351	—
反応物	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid	HCID 71279620	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-isoxazol-3-yl-ethyl)-amide	HCID 71285979	95%

反応手順

A round-bottomed flask was charged with 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.23 mmol) and 1-isoxazol-3-yl-ethylamine hydrochloride (crude from Step 3, 81 mg, 0.41 mmol). DMF (1.1 ml) was added followed by N,N-diisopropylethylamine (0.26 ml, 1.49 mmol) and HATU (95 mg, 0.25 mmol). The yellow solution was stirred at room temperature for 48 h. Water was added and the resulting suspension was filtered. The solid was washed with water and petroleum ether then dried under high vacuum to afford 115 mg (95%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-isoxazol-3-yl-ethyl)-amide as an off-white powder.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08658646B2
出典データセット	uspto-grants-2014_02
ORD ID	ord-5173b388b0894a9b8bb3203034ab51ad
出典メモ	uspto-grants-2014_02