3-Aminopyridine → 4-oxo-N-(pyridin-3-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	3-Aminopyridine	HCID 10009	—
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	4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid	HCID 58477218	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-oxo-N-(pyridin-3-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide	HCID 58477212	23%

Reaction Steps

A mixture of 4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid 35 (0.5 g, 1.5 mmol), 3-aminopyridine 36 (0.28 g, 3 mmol), HATU (1.14 g, 3 mmol) and DIPEA (0.78 g, 6 mmol) in DMF (4 mL) was stirred at room temperature for 12 h. The reaction mixture was filtered and the solid was washed with H2O and dried under vacuum to give Compound 224 as a yellow solid (0.13 g, 23% yield). MS (ESI) calcd for C22H13F3N2O3: 410.09. found: 411 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987258B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-d39bce9636a04980bfbaa002d3e27fe8
Source note	uspto-grants-2015_03