N,N-Dimethylethylenediamine → 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylethylenediamine	HCID 66053	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Chloropyridine-2-carboxylic acid	HCID 230890	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-chloro-N-(2-(dimethylamino)ethyl)picolinamide	HCID 43088258	108.4%

Reaction Conditions

Temperature	33 °C

Reaction Steps

4-Chloropicolinic acid (0.50 g, 3.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.67 g, 3.5 mmol) and 1-hydroxybenzotriazole hydrate (0.53 g, 3.5 mmol) were dissolved in DMF (6 mL). N1,N1-dimethylethane-1,2-diamine (0.381 mL, 3.49 mmol) and DIEA (0.62 mL, 3.5 mmol) were added, and the reaction was stirred at 33° C. overnight. The solution was cooled, diluted with water and extracted with methylene chloride. The organic layer was dried and concentrated to give the crude 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide (0.79 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08362037B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-40fb5bdcbbc84ab48721f0cba0d8281c
Source note	uspto-grants-2013_01