N,N'-Dimethylethylenediamine → 6-[6-((R)-3-amino-pyrrolidin-1-yl)-pyridin-3-yl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-one	HCID 57649519	—
Reactant	[(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amine	HCID 66673109	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ammonium Hydroxide	HCID 14923	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-[6-((R)-3-amino-pyrrolidin-1-yl)-pyridin-3-yl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one	HCID 24758102	64%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Degass a mixture of 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (374 mg, 1.43 mmol), [(R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amine (404 mg, 1.43 mmol) and cesium carbonate (932 mg, 2.86 mmol) in 1,4-dioxane (20 mL). Add copper (I) iodide (162 mg, 851 μmol) and sym-dimethylethylene diamine (150 mg, 1.70 mmol). Heat the mixture at 100° C. overnight. Dilute with concentrated NH4OH (5 mL) and water (50 mL) and CH2Cl2. Separate the organics and dry with Na2SO4, filter, and concentrate. Purify using chromatography (0 to 10% MeOH/CH2Cl2) to afford 0.384 g (64%) of 6-[6-((R)-3-amino-pyrrolidin-1-yl)-pyridin-3-yl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08101764B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-a90a691849144bcca7ea59508b39211f
Source note	uspto-grants-2012_01