Potassium Hydroxide → 1-{6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazin-3-yl}imidazolidin-2-one
Reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:6].[OH-].[K+]>C(O)CCC>[F:28][C:27]([F:30])([F:29])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[N:10]=[N:9][C:8]([N:7]3[CH2:2][CH2:3][NH:4][C:5]3=[O:6])=[CH:13][CH:12]=2)[CH2:15][CH2:16]1)=[O:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-(2-chloroethyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridazin-3-yl}urea (0.296 g, 0.650 mmol), potassium hydroxide (0.364 g, 0.650 mmol), in BuOH (20 mL) was refluxed overnight. The reaction mixture was concentrated and purified by column chromatography. The title compound was obtained as a light yellow powder in 71% yield (0.213 g). 1H NMR (300 MHz, CDCl3) δ 8.43 (d, J=9.9 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.48-1.64 (m, 2H), 7.34 (d, J=7.5 Hz, 1H), 7.01 (d, J=9.9 Hz, 1H), 4.91-5.12 (br., 1H), 4.22 (t, J=7.8 Hz, 1H), 3.82-4.03 (m, 2H), 3.43-3.65 (m, 6H), 3.31 (t, J=5.7 Hz, 2H).