Potassium Carbonate → HCID 71280821, compound

Participants

Reaction Steps

N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(5-methyl-1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (F79) (6.0 mg, 0.012 mmol), 1-bromo-2-methoxyethane (1.7 mg, 0.012 mmol) and K2CO3(5.0 mg, 0.036 mmol) in DMF (0.5 mL) was heated at 120° C. for 30 minutes. The reaction mixture was purified by preparative HPLC to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(1-(2-methoxyethyl)-5-methyl-1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (F99). 1H NMR (400 MHz, d6-DMSO) δ 10.15 (s, 1H), 10.11 (m, 1H), 8.65 (s, 1H), 8.12 (d, J=1.6 Hz, 1H), 8.06 (dd, J=2.0, 9.2 Hz, 1H), 7.88 (dd, J=0.8, 9.2 Hz, 1H), 7.85 (dd, J=2.0, 8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 4.34 (t, J=5.2 Hz, 2H), 3.89 (m, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.24 (s, 3H), 3.02-3.20 (m, 4H), 2.47 (s, 3H), 2.39 (s, 3H). MS m/z 549.1 (M+1)+.

Provenance & Evidence