Ammonia → (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide
Reaction equation
[CH3:1][N:2]([C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O:14]CC)=O)=[N:10][N:11]=2)[N:8]=1.[NH3:25]>>[CH3:1][N:2]([C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([NH2:25])=[O:14])=[N:10][N:11]=2)[N:8]=1Participants
3
Procedure
A solution of compound (S)-ethyl 6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate (0.5 g, 1.5 mmol) in 5 mL of methanolic ammonia (7N) was stirred for 0.5 h at room temperature. The mixture was concentrated in vacuum to give product (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide as a yellow solid (0.42 g, 92%). LRMS (M+H+) m/z: calcd 297.15; found 297. 1H NMR (300 MHz, CDCl3): δ 8.11 (br, 1H), 8.05-8.02 (d, J=9 Hz, 1H), 7.40-7.29 (m, 5H), 7.13-7.10 (d, J=9 Hz, 1H), 6.47 (br, 1H), 5.57-5.55 (q, 1H), 2.97 (s, 3H), 1.71-1.69 (d, 3H).