Pyridine → HCID 67440984, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 165 (400 mg, 0.914 mmol) and pyridine (0.222 mL, 2.74 mmol) in DMF (10 mL) at 0° C. under nitrogen was added phenyl chloroformate (0.287 mg, 2.286 mmol) and the reaction mixture was stirred at 0° C. for 2 hrs. Cyclopropylamine (0.322 mL, 4.57 mmol) was added and the reaction mixture was heated at 55° C. for 5 hrs. The reaction mixture was partitioned between EtOAc and saturated sodium bicarbonate solution, then washed with saturated ammonium chloride solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (eluent EtOAc to 20% MeOH in EtOAc) to afford title compound 166 (250 mg, 53% yield) as a white solid. 1H NMR (400 MHz. DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.44 (d, J=5.48 Hz, 1H), 8.35 (s, 1H), 8.035 (s, 1H), 7.74 (m, 1H), 7.70 (s, 1H), 7.35 (t, J=8.99 Hz, 1H), 7.19 (d, J=8.99 Hz, 1H), 6.55 (m, 2H), 4.28 (t, J=5.87 Hz, 2H), 3.59 (t, J=5.86 Hz, 2H), 3.17 (t, J=6.84 Hz, 2H), 2.55 (m, 1H), 2.15 (t, J=7.83 Hz, 2H), 1.86 (m, 2H), 0.64 (m, 2H), 0.42 (m, 2H). MS (m/z)=521.38 (M+H)

Provenance & Evidence