Diisopropylethylamine → N-{5-[(cyclopropylcarbonyl)amino]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide

https://huagongshe.com/reaction/1921294

Participants

Role	Name	HCID	Charge
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	N-(3-amino-4-methylphenyl)cyclopropanecarboxamide	HCID 24693537	—
Reactant	1-(2,6-Dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid	HCID 65501190	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-{5-[(cyclopropylcarbonyl)amino]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide	HCID 59234680	51.9%

Reaction Steps

To a solution of 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (30 mg) in DMF (0.6 mL) were added N-(3-amino-4-methylphenyl)cyclopropanecarboxamide (30 mg), HATU (60 mg) and iPr2NEt (62 mg) successively, and the mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was diluted with EtOAc (3 mL), and the resulting mixture was washed with 1 M HCl (3 mL×2), saturated aqueous NaHCO3 (3 mL×2) and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was triturated with 10% MeOH in CH2Cl2, and the precipitates produced were collected by filtration to give N-{5-[(cyclopropylcarbonyl)amino]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide (25 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08173684B2
Source dataset	uspto-grants-2012_05
ORD ID	ord-b399c39ab62a47ada02cf5fdd4ab66cd
Source note	uspto-grants-2012_05