Semicarbazide → [(E)-1-[3-[(1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[NH:24]([C:26]([NH2:28])=[O:27])[NH2:25]>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18](/[C:21](=[N:25]/[NH:24][C:26]([NH2:28])=[O:27])/[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-(3-((1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (40.0 mg, 0.09 mmol) and hydrazinecarboxamide (19.47 mg, 0.26 mmol) in 10 mL THF was stirred at 40° C. for overnight. Solvent was removed in vacuo. The crude product was purified on flash chromatography (DCM:MeOH=20:1) to give the title compound as a white solid (29.0 mg, 88%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.71 (s, 1H), 8.18 (d, 1H), 7.95 (m, 2H), 7.69 (s, 1H), 7.60 (s, 1H), 7.75 (d, 1H), 7.40 (dd, 1H), 6.76 (bs, 2H), 4.41 (s, 2H), 3.99 (s, 3H), 2.29 (s, 3H). LCMS (method A): [MH]+=363, tR=4.42 min.