Hydrochloric Acid → 3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridine-8-carboxaldehyde
반응식
C([O:3][CH:4](OCC)[C:5]1[C:6]2[N:7]([C:11]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:12]([CH3:14])[N:13]=2)[CH:8]=[CH:9][CH:10]=1)C.Cl>CC(C)=O>[CH2:25]([CH:24]([C:23]1[C:18]2[N:19]([C:15]([C:11]3[N:7]4[CH:8]=[CH:9][CH:10]=[C:5]([CH:4]=[O:3])[C:6]4=[N:13][C:12]=3[CH3:14])=[C:16]([CH3:30])[N:17]=2)[N:20]=[C:21]([CH3:29])[CH:22]=1)[CH2:27][CH3:28])[CH3:26]참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
A solution of 3-(8-diethoxymethyl-2-methyl-imidazo[1,2-a]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (2.33 g, 5.20 mmol) in acetone (25 mL) is treated with 5 M HCl (1.0 mL, 5 mmol) and the resulting solution is refluxed for 4 h. The organic solvent is removed in vacuo; the residue is diluted with H2O (100 mL), the pH is adjusted to 8-9 using sat. NaHCO3; the mixture is extracted with EtOAc (2×100 mL); dried with Na2SO4; filtered and concentrated, and purification of the crude material by silica gel chromatography gives the title compound (1.39 g, 3.72 mmol, 71%). 1H NMR (CDCl3): δ. 0.92 (t, J=7.5 Hz, 3H), 0.93 (t, J=7.5 Hz, 3H), 1.81-1.95 (m, 4H), 2.43 (s, 3H), 2.44 (s, 3H), 2.51 (s, 3H), 3.30-3.42 (m, 1H), 6.76 (s, 1H), 6.91 (t, J=7.0 Hz, 1H), 7.74 (dd, J=7.0, 1.3 Hz, 1H), 7.78 (dd, J=7.0, 1.3 Hz, 1H), 10.84 (s, 1H) ppm. ES-MS (m/z): calcd for C22H25N5O (M+H)+: 376.5. found: 376.2.