1,1'-Carbonyldiimidazole → HCID 46199245, compound

Participants

Reaction Steps

5-(4-(ethylsulfonyl)piperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (Compound I-19) CDI (102.8 mg, 0.6342 mmol) was added to a solution of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (100 mg, 0.3171 mmol) and N′-hydroxybenzamidine (86.35 mg, 0.6342 mmol) in DMF (3.000 mL) and the resulting solution stirred at RT for 3 hours and then heated at 100° C. overnight. The mixture was allowed to cool, poured in water and extracted with EtOAc. The organic extract was washed with water (2×), brine, dried over Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A 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 bright yellow solid (53.6 mg, 30% Yield). 1H NMR (400.0 MHz, DMSO) d 1.24 (3H, t), 3.11 (2H, q), 3.33 (4H, m), 3.55 (4H, m), 7.18 (2H, br s), 7.59-7.66 (3H, m), 8.19 (2H, m), 8.42 (1H, s) ppm; MS (ES+) 416

Provenance & Evidence