Anthranilamide → 2-(2,2-Difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Anthranilamide	HCID 6942	—
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	Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate	HCID 66609989	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(2,2-Difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide	HCID 66610694	75.7%

Reaction Steps

To a mixture of sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate (100 mg, 0.47 mmol), HATU (213 mg, 0.56 mmol) and 2-aminobenzamide (77 mg, 0.56 mmol) was added DMF (2 mL) and the mixture was stirred overnight at rt. The mixture was partitioned between saturated aq ammonium chloride and EtOAc, and the organic layer was concentrated. The residue was purified by silica gel chromotography eluting with 2-10% MeOH/DCM to afford 2-(2,2-difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide as an oil (110 mg, 74%). LC-MS (ESI) m/z 332 (M+Na)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08633207B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-39196647f39e469799b3182b99116ba6
Source note	uspto-grants-2014_01