Pyridine → HCID 67440529, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 156 (900 mg, 2.430 mmol) and pyridine (0.59 mL, 7.29 mmol) in DMF (10 mL) at 0° C. under nitrogen was added phenyl chloroformate (951 mg, 6.07 mmol) and the reaction mixture was stirred at 0° C. for 2 hrs. Cyclopropylamine (694 mg, 12.15 mmol) was added and the reaction mixture was heated at 55° C. for 5 hrs. The reaction mixture was then partitioned between EtOAc and saturated sodium bicarbonate solution. The organic phase was collected then washed a saturated ammonium chloride solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (eluent EtOAc to 30% MeOH in EtOAc) to afford title compound 157 (300 mg, 23% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.43 (d, J=5.47 Hz, 1H), 8.33 (s, 1H), 8.03 (s, 1H), 7.72 (m, 1H), 7.70 (m, 1H), 7.41 (m, 1H), 7.35 (t, J=9.19 Hz, 1H), 7.19 (m, 1H), 6.54 (m, 2H), 4.34 (m, 4H), 2.53 (m, 1H), 2.49 (m, 1H), 0.65 (m, 2H), 0.54 (m, 2H), 0.43 (m, 2H), 0.36 (m, 2H). MS (m/z)=537.58 (M+H).

Provenance & Evidence