Dimethyl Sulfoxide → HCID 22240510, compound

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfoxide	HCID 679	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Benzyl 3-oxopiperazine-1-carboxylate	HCID 736777	—
Reactant	HCID 67242817	HCID 67242817	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 22240510	HCID 22240510	43.4%

Reaction Conditions

Temperature	130 °C

Reaction Steps

Part A. To ethyl-6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo (3,4-c)pyridine-3-carboxamide (0.52 g, 1.0 mmol), 4-benzyloxycarbonylpiperazin-2-one (0.32 g, 1.4 mmol), and K2CO3 (0.22 g, 1.6 mmol) was added DMSO (5 mL). The mixture was degassed with N2. CuI (38 mg, 0.2 mmol) was added and the reaction was heated to 130° C. for 18 h. The reaction was diluted with EtOAc and water, extracted with EtOAc, and dried (MgSO4). Purification by chromatography on silica gel using 5% MeOH/CH2Cl2 afforded 0.2 g (33%) of a foam; Mass Spec (M+H)+ 624.6.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06989391B2
Source dataset	uspto-grants-2006_01
ORD ID	ord-2fe82f6b38ea4cf48eadade5fd45f4c7
Source note	uspto-grants-2006_01