1H-Benzimidazol-4-ylboronic acid → HCID 68194804, compound

Participants

Role	Name	HCID	Charge
Reactant	1H-Benzimidazol-4-ylboronic acid	HCID 45077856	—
Reactant	2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one	HCID 86651560	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	HCID 68194804	HCID 68194804	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 50 mg, 0.208 mmol), 1H-benzo[d]imidazol-4-ylboronic acid (71.5 mg, 0.441 mmol), and PdCl2(dppf) (7.60 mg, 10.39 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.10-3.19 (m, 1H), 3.50-3.59 (m, 2H), 3.99 (d, J=3.28 Hz, 1H), 4.18 (dd, J=11.24, 3.66 Hz, 1H), 4.43 (dd, J=10.61, 3.79 Hz, 1H), 4.59-4.71 (m, 1H), 7.49-7.67 (m, 1H), 7.90 (d, J=8.08 Hz, 1H), 8.03 (s, 1H), 8.39 (d, J=7.83 Hz, 1H), 9.23 (br s, 1H), 11.03 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C16H14N6O2, 323.12. found 323.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791107B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-83a1a2d620dd47f88f3281a5fb61daa7
Source note	uspto-grants-2014_07