5-Methoxy-o-toluidine → HCID 71241065, compound

Participants

Reaction Steps

5′-[2-(5-Methoxy-2-methyl-phenylamino)-oxazol-5-yl]-[1,3′]bipyridinyl-2-one 221 was prepared as described for I-f above from 5′-(2-Chloro-oxazol-5-yl)-[1,3′]bipyridinyl-2-one VIII-c (68 mg, 0.250 mmol), and 5-methoxy-2-methylaniline (35 mg, 0.250 mmol) in iPrOH (3 mL) to afford the title compound 221 after column chromatography (SiO2; eluting with 2% to 5% EtOH in DCM) as an orange solid (28 mg, 30%). (300 MHz, CDCl3) δ 8.83 (d, J=1.9 Hz, 1H), 8.45 (d, J=2.3 Hz, 1H), 7.93 (t, J=2.1 Hz, 1H), 7.73 (d, J=2.4 Hz, 1H), 7.41 (m, 1H), 7.34 (m, 1H), 7.30 (s, 1H), 7.07 (d, J=8.3 Hz, 1H), 6.78 (s, 1H), 6.68 (d, J=9.3 Hz, 1H), 6.55 (dd, J=8.3, 2.5 Hz, 1H), 6.30 (t, J=5.6 Hz, 1H), 3.81 (s, 3H), 2.25 (s, 3H). ESL MS m/z 375 (M+H)+. Retention time=2.99 min (method 1).

Provenance & Evidence