Pyridine → HCID 67442569, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 153 (203 mg, 0.449 mmol) and pyridine (0.109 mL, 1.346 mmol) in DMF (10 mL) at 0° C. under nitrogen was added phenyl chloroformate (1.76 mg, 1.121 mmol) and the reaction mixture was stirred at 0° C. for 2 hrs. Cyclopropylamine (128 mg, 2.243 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 a saturated ammonium chloride solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (eluent EtOAc to 30% MeOH in EtOAc) to afford title compound 154 (30 mg, 12% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.43 (s, J=5.48 Hz, 1H), 8.33 (s, 1H), 7.99 (s, 1H), 7.74 (m, 1H), 7.67 (s, 1H), 7.60 (bs, 1H), 7.32 (t, J=8.99 Hz, 1H), 7.22 (m, 1H), 6.63 (d, J=5.48 Hz, 1H), 4.25 (t, J=6.46 Hz, 2H), 2.73 (t, J=6.46 Hz, 2H), 2.55 (m, 1H), 2.45 (m, 4H), 2.28 (m, 4H), 2.12 (s, 3H), 0.61 (m, 2H), 0.40 (m, 4H). MS (m/z)=536.54 (M+H).

Provenance & Evidence