Diisopropylethylamine → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(1-methylcyclopropyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

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-Methylcyclopropanamine	HCID 11651149	—
反応物	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid	HCID 71279639	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(1-methylcyclopropyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 71279826	54.9%

反応手順

A solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (70 mg, 0.23 mmol), 1-methylcyclopropanamine (21 mg, 0.29 mmol), HATU (110 mmol, 0.29 mmol) and DIPEA (46 mg, 0.36 mmol) in 6 mL of DMF was stirred at room temperature for 16 hours. The solvent was evaporated at 70° C. under reduced pressure and the residue was triturated with dichloromethane (10 mL), methanol (10 mL) then decanted and dried to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(1-methylcyclopropyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (45 mg, 54.9%) as a white solid. MS: (M+H)+=365; 1H NMR (300 MHz, DMSO): δ 9.09 (s, 1H), 8.54 (s, 1H), 8.48-8.42 (m, 2H), 7.71 (dd, 1H, J=9.9, 2.1 Hz), 7.25-7.24 (m, 1H), 4.16 (s, 3H), 1.49 (s, 3H), 0.81 (brs, 2H), 0.80 (brs, 2H).

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-4c72084e5220463983a46bb21182b92d
出典メモ	uspto-grants-2014_02