Pyridine → HCID 86658600, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 370 (102 mg, 0.359 mmol) and pyridine (0.058 mL, 2 eq, 0.718 mmol) in THF (5 ml)/DMF (2 ml) at 0° C. under nitrogen was added phenyl chloroformate (0.068 mL, 1.5 eq, 0.538 mmol) and the reaction mixture was stirred at 0° C. for 1 hr. Cyclopropylamine (102 mg, 5 eq, 1.794 mmol) was added and the reaction mixture was heated at 55° C. for 3 hrs. The mixture was then cooled to RT, diluted with EtOAc then washed sequentially with saturated solutions of NH4Cl, NaHCO3 and brine. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified via column chromatography (eluent EtOAc to 40% MeOH in EtOAc) to afford the title compound 371 (100 mg, 76% yield) as an off-white powder after trituration with Et2O. MS (m/z): 368.23 (M+H)

Provenance & Evidence