2-Bromo-6-(2,4-dichloro-phenyl)-cyclohexanone → [4-(2,4-Dichloro-phenyl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine
反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[C:21]1=O>C(O)C>[Cl:33][C:27]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:26]=1[CH:22]1[C:21]2[N:18]=[C:16]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[S:17][C:20]=2[CH2:25][CH2:24][CH2:23]1参加物
4
実験手順
A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (62 mg, 0.24 mmol) and of crude 2-bromo-6-(2,4-dichloro-phenyl)-cyclohexanone (79 mg, 0.25 mmol) in ethanol (2 mL) was heated to reflux under an atmosphere of nitrogen for 3 days. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound (43 mg, 37%) as an off-white solid. MS ISP (m/e): 485.3/487.3 (100/73) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.00 (s, 1H), 7.47 (s, 1H), 7.39 (s, 1H), 7.11 (m, 2H), 6.89 (m, 2H), 6.75 (d, 1H), 4.47 (m, 1H), 3.60 (s, 3H), 2.76 m, 2H), 2.38 (s, 3H), 2.22 (m, 1H), 1.86 (m, 3H).