Cyclopropanecarboxylic acid → N-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)cyclopropanecarboxamide

https://huagongshe.com/reaction/520298

Participants

Role	Name	HCID	Charge
Reactant	Cyclopropanecarboxylic acid	HCID 15655	—
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-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one	HCID 52911268	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)cyclopropanecarboxamide	HCID 117777391	72.5%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a mixture of cyclopropanecarboxylic acid (180 mg, 2.0 mmol), HATU (570 mg, 1.5 mmol) and DIPEA (390 mg, 3.0 mmol) in DCM (8 mL) was added 3-amino-5-bromo-1-methylpyridin-2(1H)-one (230 mg, 1.12 mmol). The reaction mixture was stirred at 25° C. for 5 hours. The resulting mixture was evaporated under reduced pressure and the residue was purified on a silica-gel column chromatography eluting with 20:1 DCM/methanol to afford the 102a (220 mg, 72%). MS-ESI: [M+H]+ 270.1

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09326985B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-0c50b0439d7d4f13ad1bf8230a04b2f0
Source note	uspto-grants-2016_05