Semicarbazide hydrochloride → [(E)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea
Reaction equation
[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12](=O)[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Cl.[NH:27]([C:29]([NH2:31])=[O:30])[NH2:28]>CO>[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9](/[C:12](=[N:28]/[NH:27][C:29]([NH2:31])=[O:30])/[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (100 mg, 0.295 mmol) and hydrazinecarboxamide hydrochloride (44.3 mg, 0.589 mmol) in MeOH was stirred at room temperature for overnight. Solvent was evaporated and the residue was dissolved in a small amount of MeOH. Solid was filtered and dried to give the title compound as a white solid (90 mg, 75%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.90 (s, 1H), 9.06 (d, 1H), 8.62 (d, 1H), 8.49 (m, 2H), 8.34 (d, 1H), 8.20 (d, 1H), 8.03 (d, 1H), 7.70 (m, 1H), 6.82 (broad, 2H), 2.07 (s, 3H). LCMS (method B): [MH]+=397.1, tR=2.08 min.