Cesium carbonate → (R)-2,2-difluoro-1-(2-((7-(4-(4-methylpiperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholino)ethanone

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine	HCID 17998905	—
Reactant	(R)-1-(2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholino)-2,2-difluoroethanone	HCID 86717395	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	(R)-2,2-difluoro-1-(2-((7-(4-(4-methylpiperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholino)ethanone	HCID 86717394	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a solution of (R)-1-(2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholino)-2,2-difluoroethanone (72 mg, 0.2 mmol) in dioxane/H2O (5 mL/0.5 mL) was added Cs2CO3 (98 mg, 0.3 mmol), Pd (PPh3)4 (46.2 mg, 0.04 mmol) and 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine (72.5 mg, 0.24 mmol). The mixture was stirred at 110° C. for 24 hours under N2. The reaction was filtered, concentrated and purified on column (CH2Cl2:MeOH=20:1) to give yellow solid. MS (m/z): 498 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434726B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-2759147125e54f289dbc273ee2fcfefc
Source note	uspto-grants-2016_09