Diisopropylethylamine → N-(4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromen-8-yl)thiazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Thiazolecarboxylic acid	HCID 304271	—
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	8-amino-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one	HCID 58477271	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromen-8-yl)thiazole-4-carboxamide	HCID 58477258	29.2%

Reaction Steps

8-amino-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one (178) (70 mg, 0.23 mmol) was taken up in 2 mL of DMF along with thiazole-4-carboxylic acid 3 (30 mg, 0.23 mmol), HATU (175 mg, 0.46 mmol) and DIEA (80 μL, 0.46 mmol). The reaction mixture was stirred at room temperature for 18 h. It was then diluted with 5 mL of H2O. The resulting solids were collected by filtration, washed successively with a solution of dilute NaHCO3/MeOH (1:1), aqueous MeOH, dilute 1 N HCl/MeOH (1:1), aqueous MeOH, and then pure MeOH. After drying under high vacuum, 28 mg of Compound 204 was obtained as an off-white solid. MS (ESI) calcd for C20H11F3N2O3S: 416.04. found: 417 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987258B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-74e10d83798d46d88c32a0b763042a01
Source note	uspto-grants-2015_03