Diisopropylethylamine → HCID 49870875, compound

Participants

Reaction Conditions

Reaction Steps

6-[(S)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline (Intermediate B, 3.0 g, 8.58 mmol), KF (2.52 g, 42.9 mmol), 1-methylpiperazine-2-one hydrochloride (3.88 g, 25.7 mmol), N-ethyldiisopropylamine (5.99 mL, 35 mmol) were suspended in NMP (60 mL). The RM was stirred at 180° C. for 8.5 h. The mixture was diluted with EtOAc and washed with 1M Na2CO3 (1×) and water (2×). The aqueous was further extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography and then crystallized in EtOAc to afford the title compound as a white solid (tR 3.19 min (conditions 1), (tR 8.84 min (conditions 2), MH+=423.2, 1H-NMR in DMSO-d6: 8.94 (d, 1H); 8.45 (d, 1H); 7.84 (d, 1H); 7.63 (s, 1H); 7.59 (m, 2H); 7.08 (d, 1H); 4.98 (m, 1H); 4.02 (d, 1H); 3.73 (d, 1H); 3.60 (m, 2H); 3.31 (m, 1H); 3.25 (m, 1H); 2.80 (s, 3H); 1.88 (d, 3H)).

Provenance & Evidence