HCID 58084376, compound → [3-Amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-phenyl-methanone

Participants

Reaction Steps

1M Bromo(phenyl)magnesium in THF (823.2 μL, 0.8232 mmol) was added dropwise to a stirred solution of 3-amino-6-(4-isopropylsulfonylphenyl)-N-methoxy-N-methyl-pyrazine-2-carboxamide (100 mg, 0.2744 mmol) in anhydrous THF (6 mL) at −78° C. under an atmosphere of nitrogen. The reaction was stirred at this temperature for 30 minutes then allowed to warm to ambient temperature over 16 hours. The reaction mixture was concentrated in vacuo and residue was partitioned between DCM and water. The layers were separated and the organic extract was dried (MgSO4) and concentrated in vacuo. The 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 as a yellow solid (49 mg, 42% Yield). NMR (400.0 MHz, DMSO) δ 1.16 (d, 6H), 3.44 (sept, 1H), 7.55-7.59 (m, 2H), 7.66 (m, 1H), 7.90 (d, 2H), 7.95-7.97 (m, 2H), 8.07 (br s, 2H), 8.18 (d. 2H) and 9.10 (s, 1H) ppm; (ES+) 382.0.

Provenance & Evidence