Diisopropylethylamine → 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide

참여 물질

역할	이름	HCID	투입량
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	(S)-1-methoxypropan-2-amine hydrochloride	HCID 54596079	—
반응물	2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid	HCID 58438525	—
용매	Water	HCID 962	—
용매	Dimethylformamide	HCID 6228	—
생성물	2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide	HCID 86677909	90.9%

반응 단계

In a round-bottomed flask were combined 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (120 mg, 0.32 mmol) and (S)-1-methoxypropan-2-amine hydrochloride (61 mg, 0.49 mmol). DMF (1.5 mL) was added followed by N,N-diisopropylethylamine (0.15 mL, 0.86 mmol) and HATU (135 mg, 0.36 mmol). The yellow reaction mixture was stirred at room temperature overnight then water was added. The resulting suspension was filtered and the filter cake was washed with water and petroleum ether then dried under high vacuum to provide 129 mg (90%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide as an off-white powder.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08658646B2
출처 데이터셋	uspto-grants-2014_02
ORD ID	ord-03920af917dd49acad8e1aae70f45c75
출처 메모	uspto-grants-2014_02