Sulfuric Acid → HCID 86685627, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of tert-tutyl ((1S,2R)-2-((6-chloro-5-cyanopyrazin-2-yl)amino)cyclohexyl)carbamate (100 mg, 0.28 mmol), 3-aminopyridine (53 mg, 0.56 mmol), powder cesium carbonate (360 mg, 1.12 mmol), BINAP (37 mg, 0.06 mmol), Pd(OAc)2 (14 mg, 0.06 mmol) in 20 mL dioxane was degassed with argon stream. It was stirred in argon atmosphere at 110° C. for 2 h. The mixture was cooled, diluted with 100 mL EtOAc, vigorously stirred, and filtered through celite. The filtrate was concentrated and subjected to silica flash column with 0-70% EtOAc in hexane to isolate the coupling product. It was then stirred in 6 mL TFA and 1 mL conc. H2SO4 at 80° C. for 30 m. It was cooled in ice bath, diluted with water, filtered, and subjected to reverse phase preparative HPLC to isolate the title compound (103 mg). MS found for C16H21N7O as (M+H)+328.5. UV: λ=230, 259, 301 nm. 1H NMR: (CD3OD) δ 9.50 (1H, s), 8.56 (1H, d, J=8.8 Hz), 8.42 (1H, d, J=5.6 Hz), 7.95 (1H, dd, J=8.8; 5.6 Hz), 7.75 (1H, s), 4.57 (1H, m), 3.70 (1H, m), 1.95-1.58 (8H, m) ppm.

Provenance & Evidence