Pyridine → HCID 67443712, compound

Participants

Reaction Steps

To a solution of amine 268 (1.7 g, 3.98 mmol) in DMF (7 mL) was added pyridine (0.55 mL, 6.77 mmol) at RT and the resultant solution was stirred for 10 min under Ar atmosphere. Phenyl chloroformate (0.75 mL, 5.97 mmol) was added at 0° C. and the mixture was stirred at RT for 40 min. Cyclopropylamine (1.1 mL, 15.9 mmol) was added to the mixture, and the reaction mixture was warmed to 50° C. and stirred for 2 hours. The mixture was then cooled to RT then poured into water (150 mL) and stirred for 30 min. The precipitate was collected by filtration, washed with water and dried. The crude product was triturated with EtOActo afford title compound 269 (1.75 g, 86% yield) as a pale-violet solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 8.70 (br, 1H), 8.45 (d, J=5.4 Hz, 1H), 7.91 (s, 1H), 7.72 (dd, J=13.5, 2.4 Hz, 1H), 7.35 (t, J=9.0 Hz, 1H), 7.23 (m, 1H), 6.62 (d, J=5.4 Hz, 1H), 6.56 (br, 1H), 2.60-2.40 (m, 1H), 0.70-0.60 (m, 2H), 0.48-0.35 (m, 2H).

Provenance & Evidence