Cyanoacrylic acid → N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl)-2-cyanoacrylamide

Participants

Role	Name	HCID	Charge
Reactant	Cyanoacrylic acid	HCID 27488	—
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	3-(6-(2-aminoethoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochloride	HCID 118116894	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl)-2-cyanoacrylamide	HCID 118116912	67.4%

Reaction Steps

A mixture of 3-(6-(2-aminoethoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one 103a (480 mg, 1.42 mmol), 2-cyanoacrylic acid (790 mg, 2.84 mmol), DIPEA (1.2 mL, 7.12 mmol) and HATU (810 mg, 2.13 mmol) in DCM (10 mL) was stirred at rt for 16 h. The reaction mixture was concentrated and purified by silica gel chromatography (PE/EA=1/2) to give N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl)-2-cyanoacrylamide 117a (400 mg, 67%) as green solid. ESI-LCMS: m/z=420.0

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09260415B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-4ab4a35ccd2d4bfdacd6baebc1f6c791
Source note	uspto-grants-2016_02