Nitrogen → N-[4-(2,4-difluorophenoxy)-3-(7-methyl-8-oxo-[1,2,4]triazolo[4,3-a]pyrazin-5-yl)phenyl]ethanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	5-Bromo-7-methyl-[1,2,4]triazolo[4,3-a]pyrazin-8-one	HCID 118021723	—
Reactant	N-(4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanesulfonamide	HCID 124081953	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-[4-(2,4-difluorophenoxy)-3-(7-methyl-8-oxo-[1,2,4]triazolo[4,3-a]pyrazin-5-yl)phenyl]ethanesulfonamide	HCID 118022239	49.3%

Reaction Steps

The title compound of Example 235, step 2 (40 mg, 0.175 mmol), N-[4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide (77 mg, 0.175 mmol), K3PO4 (93 mg, 0.438 mmol) and Pd(dppf)Cl2 (13 mg, 0.018 mmol) in dioxane (2 mL) and H2O (1 mL) was N2 purged and microwaved at 70° C. for 2 h. Preparative HPLC gave the title compound (38.75 mg, yield: 49.3%) as an off-white solid. 1H NMR (CDCl3, 400 MHz): δ 8.60 (s, 1H), 7.64 (d, J=2.8 Hz, 1H), 7.45 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 7.10-7.05 (m, 1H), 6.99-6.88 (m, 3H), 6.74 (d, J=8.8 Hz, 1H), 3.67 (s, 3H), 3.18 (q, J=7.2 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H). LCMS: 462.0 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-57cc6187288240b18a8331a5a8c7b438
Source note	uspto-grants-2015_08