Ammonia → 4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-b]pyridazin-6-yl)pyridin-2(1H)-one

https://huagongshe.com/reaction/2203026

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one	HCID 57497864	—
Reactant	6-Bromo-2-cyclopropyl-3-methylimidazo[1,2-b]pyridazine	HCID 89690290	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-b]pyridazin-6-yl)pyridin-2(1H)-one	HCID 89690368	28%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (108 mg), 6-bromo-2-cyclopropyl-3-methylimidazo[1,2-b]pyridazine (150 mg), N,N′-dimethyl-1,2-ethanediamine (81 mg), CuI (87 mg), potassium carbonate (190 mg) and DMSO (3 ml) was heated at 150° C. for 1 h under microwave irradiation. The mixture was poured into 28% NH3 solution, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4, concentrated in vacuo, and purified by column chromatography (hexane/EtOAc), followed by crystalization from EtOAc-hexane to give the title compound (52.3 mg) as pale yellow crystals.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365540B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-7029be4f1acd4b589352e7051ad47a34
Source note	uspto-grants-2016_06