N,N'-Dimethylethylenediamine → HCID 16064037, compound

https://huagongshe.com/reaction/2074924

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-(3,5-Bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(4-fluoro-2-methylphenyl)pyrid-3-yl)-N,2-dimethylpropanamide	HCID 23502784	—
Reactant	HCID 51898145	HCID 51898145	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 16064037	HCID 16064037	21.6%

Reaction Steps

A solution of (9aS)-octahydro-1H-pyrrolo[1,2-a][1,4]diazepin-1-one (Polish Journal of Chemistry, 59(10-12), 1243-6; 1985) (31 mg, 0.201 mmol), 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide [WO 2005/002577] (53 mg, 0.0996 mmol), N,N′-dimethyethylendiamine (224, 0.207 mmol), copper(I) iodide (38 mg, 0.200 mmol) and caesium carbonate (65 mg, 0.199 mmol) in 3 mL of dioxane was heated to 100° C. in a sealed vial overnight. Heating was continued for additional 2 days. It was diluted with 10 mL of EtOAc and extracted with water. The organics were dried (Na2SO4) and the solvent removed. The product was isolated by flash chromatography (silica, cyclohexane:EtOAc 90:10 to 30:70). Thus were obtained 14 mg of the target compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07919491B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-88e85ce139184a33968974f66ceb48e8
Source note	uspto-grants-2011_04