3-Butyn-2-amine, 2-methyl- → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2-methylbut-3-yn-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	3-Butyn-2-amine, 2-methyl-	HCID 76319	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid	HCID 71279639	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2-methylbut-3-yn-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide	HCID 86677992	23.6%

Reaction Steps

A mixture of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (70 mg, 0.225 mmol), 2-methylbut-3-yn-2-amine (28 mg, 0.338 mmol), HATU (171 mg, 0.45 mmol) and DIEA (58 mg, 0.45 mmol) in DMF (3 mL) was stirred at room temperature for 16 hours. Then the mixture was poured into water and filtered to give the crude product. The crude compound was then washed with MeOH to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2-methylbut-3-yn-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (20 mg, 23.5%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658646B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-f3f52c0666b94a278cb018860fd14320
Source note	uspto-grants-2014_02