Hydrochloric Acid → HCID 56848818, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL microwave vial with stirbar was added 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine (25.00 mg; 0.08 mmol; 1.00 eq.) and 6-amino-2,2-difluoro-4H-benzo[1,4]oxazin-3-one (16.43 mg; 0.08 mmol; 1.05 eq.). The vial was sealed and flushed with N2 and the reagents were dissolved in NMP (1.00 ml). Hydrogen chloride in dioxane (0.02 ml; 4.00 M; 0.08 mmol; 1.05 eq.) was added and the reaction mixture was heated to 150° C. in a microwave reactor for 1 h. The reaction mixture was cooled to room temperature and quenched with NaOH(aq), extracted with EtOAc, dried (MgSO4) and concentrated on a rotary evaporator. The crude mixture was purified by Biotage chromatography (2-10% MeOH/CH2Cl2 15 column vol.; 10% MeOH/CH2Cl2 5 column vol.) to afford the title compound as a beige solid (10 mg, 26%). (HPLC (method F): 90%, RT: 4.69 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 11.99 (s, 1H), 9.14 (s, 1H), 8.17 (d, J=5.5, 1H), 7.57 (s, 1H), 7.35 (d, J=8.8, 1H), 7.22 (s, 2H), 7.08-7.00 (m, 2H), 6.88 (d, J=5.5, 1H), 3.85 (s, 6H), 3.72 (s, 3H); MS (m/z) 484 [M+H]+, RT: 2.9 min.

Provenance & Evidence