Benzenesulfonamide → N-(3-amino-6-(4-(methylsulfonyl)phenyl)pyrazin-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

3-bromo-5-(4-methylsulfonylphenyl)pyrazin-2-amine (0.05 g, 0.152 mmol), benzene sulfonamide (0.12 g, 0.762 mmol), (1R,2R)-cyclohexane-1,2-diamine (0.017 g, 0.152 mmol), cuprous iodide (0.058 g, 0.305 mmol) and K2CO3 (0.042 g, 0.305 mmol) were combined together in dioxane (4 mL) and heated for 15 minutes under microwave conditions at 120° C. and then 140° C. for a further 20 minutes. The reaction mixture was concentrated in vacuo, and the residue was partitioned between DCM and water. The layers were separated and the aqueous further extracted with DCM. The combined organic extract was dried (MgSO4), filtered and concentrated in vacuo. This material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried to give the title compound (3.9 mg, 3.65% Yield). H1 NMR (400.0 MHz, DMSO) δ 8.34 (s, 1H), 8.04-8.01 (m, 2H), 7.88 (d, J=8.6 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H), 7.67-7.64 (m, 3H) and 3.23 (s, 3H). MS (ES+) 405.0

Provenance & Evidence