Ethanol → 4,5,6,7-Tetrahydro-N-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-4-(2-methoxyphenyl)-2-benzothiazolamine
Reaction equation
[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][CH:29]=[CH:28][CH:27]=2)[C:21]1=[O:32].[CH2:33](O)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][C:28]3[CH2:29][CH2:30][CH2:31][CH:26]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:20][C:21]=4[O:32][CH3:33])[C:27]=3[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1Participants
4
Procedure
A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (43 mg, 0.16 mmol) and of crude 2-bromo-6-phenyl-cyclohexanone (49 mg, 0.17 mmol) in ethanol (2 mL) was heated to reflux under an atmosphere of nitrogen for 2 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 (15 mg, 21%) as a yellow gum. MS ISP (m/e): 447.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.59 (s, 1H), 7.29 (s, 1H), 7.07-7.18 (m, 2H), 6.82-6.88 (m, 4H), 6.65 (d, 1H), 4.49 (m, 1H), 3.84 (s, 3H), 3.57 (s, 3H), 2.89 (m, 2H), 2.88 (s, 3H), 2.14 (m, 1H), 1.70-1.91 (m, 3H).
Workup
- temperatureto reflux under an atmosphere of nitrogen for 2 days
- customwas evaporated under reduced pressure
- customthe residue was purified by reversed preparative HPLC
Sources & evidence
- ORD record
- ord-881ddba6e4c34e928da24847c087e357
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923450B2
Reaction notes
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