Hydrochloric Acid → 2-(4-Chloro-phenyl)-6-[6-((s)-3-dimethylamino-pyrrolidin-1-yl)-pyridin-3-yl]-6h-thieno[2,3-c]pyridin-7-one, hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
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	(3S)-1-(5-bromo-2-pyridinyl)-N,N-dimethyl-3-pyrrolidinamine	HCID 60052291	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethanol	HCID 702	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(4-Chloro-phenyl)-6-[6-((s)-3-dimethylamino-pyrrolidin-1-yl)-pyridin-3-yl]-6h-thieno[2,3-c]pyridin-7-one, hydrochloride	HCID 24759352	116.4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Combine 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (0.2575 g, 0.98 mmol), [(S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl]-dimethyl-amine (Goodfellow, V.; et. al. US 2005012853) (0.3184 g, 1.18 mmol), and Cs2CO3 (0.64 g, 1.96 mmol) in dioxane (25 mL). Degass the suspension by purging with nitrogen for 5 min. Add CuI (37 mg, 0.20 mmol) and N,N′-dimethylethylenediamine (35 mg). Stir the reaction mixture at 100° C. overnight. Cool to RT and dilute with EtOAc (100 mL). Wash with a solution of H2O/NH3.H2O (2×30 mL/2 mL). Dry the organic layer over Na2SO4, filter and concentrate. Purify the crude material by chromatography by eluting with 2% NH3.H2O, 50% CH3OH/EtOAc to provide 0.258 g. Dissolve the material in CH2Cl2 (5 mL) and treat with 1.0 M HCl in EtOH (0.57 mL) to provide 0.278 g (58%) of the title compound. LC-MS/ES m/z (35Cl) 451.2 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08101764B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-782bb23ef4914558bc98d08c8e711aac
Source note	uspto-grants-2012_01