Triethylamine → 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzoic acid, 4-amino-3-nitro-	HCID 74115	—
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	5-Amino-2,3-dimethyllutidine	HCID 66966202	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide	HCID 66966059	—

Reaction Steps

To DMF (20 mL) were added HATU (2.87 g, 7.55 mmol), 4-amino-3-nitrobenzoic acid (916 mg, 5.03 mmol), triethylamine (1.05 mL, 762 mmol) and 5-amino-2,3-dimethyllutidine (615 mg, 5.03 mmol) [J. Het. Chem. 31, 1641 (1994)]. The mixture was stirred at ambient temperature for 1 h, then at 80° C. for 18 h. The solution was decanted into ethyl acetate and extracted once with water and five times with brine, then dried, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography using a gradient of 80-100% heptane/ethyl acetate to give 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide. MS (m/z) 287.0 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08222248B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-8ef9ed8c2983408895d88b71b23fcab6
Source note	uspto-grants-2012_07