3-Aminopyridine → HCID 54596225, compound

Participants

Reaction Steps

tert-Butyl N-[5-bromo-3-[tert-butoxycarbonyl(phenyl)carbamoyl]pyrazin-2-yl]carbamate (60 mg, 0.1216 mmol), dicesium carbonate (118.9 mg, 0.3648 mmol), pyridin-3-amine (17.17 mg, 0.1824 mmol), 2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethyl-aniline (14.36 mg, 0.03648 mmol), 1,5-diphenylpenta-1,4-dien-3-one; palladium (11.14 mg, 0.01216 mmol) in toluene (06. mL) heated under microwave conditions at 130° C. for 30 minutes. The reaction mixture was filtered and the filtrate diluted with DCM (2 mL) and TFA (0.5 mL) was added. The resulting solution was stirred at ambient temperature for 30 minutes then concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 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 an yellow solid (7 mg, 19% Yield). 1H NMR (400.0 MHz, DMSO) δ 9.99 (s, 1H), 9.86 (s, 1H), 9.12 (s, 1H), 8.30 (d, J=4.8 Hz, 1H), 8.20 (d, J=3.4 Hz, 2H), 7.75 (dd, J=7.7, 16.7 Hz, 3H), 7.41-7.37 (m, 2H), 7.22 (s, 1H) and 7.14 (t, J=7.4 Hz, 2H) ppm; MS (ES+) 307.

Provenance & Evidence