Diisopropylethylamine → N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromoisonicotinic acid	HCID 222701	—
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	N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride	HCID 67125547	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide	HCID 86680169	44%

Reaction Steps

A solution of 2-bromoisonicotinic acid (160 mg, 0.792 mmol), HATU (331 mg, 0.871 mmol) and DIPEA (0.655 mL, 3.96 mmol) in DMF (8 mL) was stirred at rt for 10 min. N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride 29 (248 mg, 0.871 mmol) was added and stirred at rt for 3 h. Quenched in 3% citric acid solution and the resulting precipitate was collected. Triturating with acetonitrile gave N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide (30) (163 mg, 44%). (m/z)=468 and 470 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669256B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-a7df7cd3a7374cf785c164a317689ed3
Source note	uspto-grants-2014_03