[CH:1]([C:4]1[N:8]2[N:9]=[C:10]([CH:13]=O)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].[CH3:15][NH2:16].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH:1]([C:4]1[N:8]2[N:9]=[C:10]([CH:13]=[N:16][CH3:15])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]To a flask was added 3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine-6-carbaldehyde (0.420 g, 2.21 mmol, Preparation #2), and methylamine (40 wt % in water, 1.33 mL, 2.65 mmol) followed by MgSO4 (0.399 g, 3.31 mmol) in DCM (2 mL) to give an orange suspension. The mixture was stirred at ambient temperature for about 17 h. The mixture was filtered and concentrated in vacuo to afford the title compound (0.300 g, 67%): 1H NMR (DMSO-d6) δ 8.43 (s, 1H), 8.31 (d, 1H), 7.74 (d, 1H), 3.59 (m, 4H), 2.5 (s, 3H), 1.45 (d, 6H).
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