Diethyl Ether → 1-Methyl-3-[4-[8-(morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

Participants

Reaction Conditions

Reaction Steps

A solution of compound 51e (0.20 g, 0.29 mmol) in TFA/DCM (1:3 v/v, 5 mL) was stirred overnight at rt. The mixture was concentrated under reduced pressure, and the residue obtained was treated with Et2O (10 mL). The solids formed were collected by filtration, washed with Et2O (2×20 mL), and treated with MeOH (5 mL) and DIEA (0.5 mL). The resulting solution was stirred at 70° C. for 30 min and allowed to cool to rt. The solids formed were collected by filtration and washed with Et2O (2×20 mL) to obtain the title compound 78 as a white solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 12.30 (s, 1H), 8.21 (d, J=8.7 Hz, 1H), 8.08 (d, J=5.4 Hz, 1H), 7.85-7.92 (m, 4H), 7.76-7.67 (m, 3H), 7.55-7.50 (m, 1H), 7.41 (d, J=8.4 Hz, 1H), 6.34 (d, J=5.7 Hz, 1H), 3.92-3.85 (m, 4H), 3.78-3.70 (m, 4H), 3.39-3.34 (m, 7H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H28N8O2: 533.2 (M+H). Found: 533.3.

Provenance & Evidence