tert-Butyl piperazine-1-carboxylate → HCID 58168295, compound

Participants

Role	Name	HCID	Charge
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one	HCID 58168008	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	HCID 58168295	HCID 58168295	42.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (100 mg, 0.43 mmol), 1-Boc-piperazine (161 mg, 0.87 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and NaOtBu (167 mg, 1.73 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 50 to 100% EtOAc in hexanes to provide 178 (70 mg, 42% yield) as a yellow solid. LC-MS (M+H=381, obsd.=381).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-bed473d110564ebc9da462d991d6c932
Source note	uspto-grants-2014_05