N,N-dimethylhydroxylamine hydrochloride → 6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide

Participants

Role	Name	HCID	Charge
Reactant	N,N-dimethylhydroxylamine hydrochloride	HCID 27969	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	6-(3-Ethylureido)-4-(phenylamino)nicotinic acid	HCID 89650005	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide	HCID 89650373	—

Reaction Steps

4-anilino-6-(ethylcarbamoylamino)pyridine-3-carboxylic acid (i) (200 mg, 0.67 mmol), dimethylhydroxylamine hydrochloride (65 mg, 0.67 mmol), 4-dimethylaminopyridine (81 mg, 0.67 mmol) and N-hydroxybenzotriazole (90 mg, 0.67 mmol) were added to a dry RBF which was flushed with N2. DMF (1.5 mL) was added and the mixture stirred. 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine hydrochloride (150 mg, 0.80 mmol) was dissolved in DMF (1.5 mL) in a separate vial and this solution added to the reaction mixture at RT. The mixture was stirred overnight at RT.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09060515B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-822713183a2941bea96d1c37d5b8cf4d
Source note	uspto-grants-2015_06