Ethylmorpholine → N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4-imidazolidinecarboxamide

https://huagongshe.com/reaction/2080956

Participants

Role	Name	HCID	Charge
Reactant	Ethylmorpholine	HCID 7525	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2-Chloro-3-(trifluoromethyl)benzylamine	HCID 5224207	—
Reactant	3-Methyl-2-oxoimidazolidine-4-carboxylic acid	HCID 55300151	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4-imidazolidinecarboxamide	HCID 25097730	49.6%

Reaction Conditions

Temperature	22 °C

Reaction Steps

Crude 3-methyl-2-oxo-4-imidazolidinecarboxylic acid (˜0.63 mmol, prepared as described below) was dissolved in dimethylformamide (3 ml) and treated with 1-hydroxybenzotriazole (0.094 g, 0.69 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.132 g, 0.69 mmol), [(2-chloro-3-trifluoromethylphenyl)methyl]amine (0.145 g, 0.69 mmol) and N-ethylmorpholine (0.169 ml, 1.32 mmol). The mixture was stirred at 22° C. for 20 hours then reduced in vacuo to give a residue which was purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4-imidazolidinecarboxamide as a white solid (0.105 g). LC/MS [M+H]+=336, retention time=2.18 minutes.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07932282B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-771a5c310a1d440ebe22a39c2af1a78b
Source note	uspto-grants-2011_04