Diisopropylethylamine → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-2-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	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid	HCID 71279620	—
反応物	1-Oxazol-2-yl-ethylamine dihydrochloride	HCID 86677915	—
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-oxazol-2-yl-ethyl)-amide	HCID 71286002	97%

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 (210 mg, 0.48 mmol) and 1-oxazol-2-yl-ethylamine dihydrochloride (198 mg, 0.86 mmol). DMF (2.2 ml) was added followed by N,N-diisopropylethylamine (0.55 ml, 3.15 mmol) and HATU (199 mg, 0.52 mmol). The light yellow solution was stirred at room temperature overnight. 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 248 mg (97%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-2-yl-ethyl)-amide as a light yellow 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-ce1e004cf2f74b0b99b9ccdfa86568ee
出典メモ	uspto-grants-2014_02