2-Aminothiazole → 2-(3-(difluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-8-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	2-Aminothiazole	HCID 2155	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium Bicarbonate	HCID 516892	—
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	2-(3-(Difluoromethyl)phenyl)quinoline-8-carboxylic acid	HCID 58154684	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(3-(difluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-8-carboxamide	HCID 58154630	39%

Reaction Conditions

Temperature	40 °C

Reaction Steps

A mixture of 2-(3-(difluoromethyl)phenyl)quinoline-8-carboxylic acid (250 mg, 0.84 mmol), thiazol-2-amine (84 mg, 1.2 mmol), HATU (0.64 g, 1.68 mmol) and DIPEA (0.22 g, 1.68 mmol) in DMF (25 mL) was stirred at 40° C. for 12 hours. A saturated solution of NaHCO3 (5 mL) was added and the mixture was filtered, the residue was washed with methanol (2×5 mL) and solid was dried in vacuo to give 2-(3-(difluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-8-carboxamide as a solid. (125 mg, 39% yield) MS (ESI) calcd for C20H13F2N3OS (m/z): 381.07. found: 382 [M+1].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08685970B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-56f6e310afc34fdc9a48041e0bd185c7
Source note	uspto-grants-2014_04