Benzylamine → HCID 54597091, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (50 mg, 0.1404 mmol), benzylamine (30.09 mg, 30.67 μL, 0.2808 mmol) and Et3N (28.41 mg, 39.13 μL, 0.2808 mmol) in NMP (500 μL) were heated at 120° C. under microwave conditions for 1.5 hours. A further portion of benzylamine (225.7 mg, 230.1 μL, 2.106 mmol) was added and the reaction heated at 120° C. under microwave conditions for a further 45 minutes. The reaction mixture was diluted with water and extracted with EtOAc (×3). The combined organic extracts were dried (MgSO4), filtered 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 cream solid (22.3 mg, 42% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.16 (d, 6H), 3.41 (sept, 1H), 4.70 (d, 2H), 7.15 (br s, 1H), 7.26 (t, 1H), 7.36 (t, 2H), 7.44 (d, 2H), 7.82 (d, 2H), 7.96 (s, 1H) and 8.14 (d, 2H) ppm; MS (ES+) 383.2.

Provenance & Evidence