Triethylamine → (R)-3-(5-Methylpyridin-2-yl)-5-(methylsulfonyl)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	(1R)-1-[6-(Trifluoromethyl)(3-pyridyl)]ethylamine	HCID 55278063	—
Reactant	3-(5-Methylpyridin-2-yl)-5-(methylsulfonyl)benzoic acid	HCID 58188150	—
Solvent	Dichloromethane	HCID 6344	—
Product	(R)-3-(5-Methylpyridin-2-yl)-5-(methylsulfonyl)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)benzamide	HCID 58187963	—

Reaction Steps

Into a round-bottom flask were charged 3-(5-methylpyridin-2-yl)-5-(methylsulfonyl)benzoic acid (40% mixture with BaCl2, 250 mg, 0.34 mmol), (R)-1-(6-(trifluoromethyl)pyridin-3-yl)ethanamine (130 mg, 0.69 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (130 mg, 0.69 mmol), 1-hydroxybenzotriazole hydrate (100 mg, 0.69 mmol), triethylamine (87 mg, 0.86 mmol) and CH2Cl2 (3 mL). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified via flash chromatography to afford the desired product as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946439B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-cd936445c35b4695a3afdb20056b77dc
Source note	uspto-grants-2015_02