Benzyl Bromide → Methyl 3-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate
Reaction equation
C(Br)C1C=CC=CC=1.Br[CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15].[C:21]([C:24]1[S:28][C:27]([N:29]2[CH2:33][CH2:32][NH:31][C:30]2=[O:34])=[N:26][C:25]=1[CH3:35])(=[O:23])[CH3:22]>>[C:21]([C:24]1[S:28][C:27]([N:29]2[CH2:33][CH2:32][N:31]([CH2:10][C:11]3[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=3)[C:14]([O:16][CH3:17])=[O:15])[C:30]2=[O:34])=[N:26][C:25]=1[CH3:35])(=[O:23])[CH3:22]Participants
4
Procedure
Following the procedure as described in Example 5, making variations to replace benzyl bromide with methyl 3-(bromomethyl)benzoate to react with 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one, the title compound was obtained as a white solid in 64% yield: mp 122-124° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.99-7.93 (m, 2H), 7.52-7.40 (m, 2H), 4.53 (s, 2H), 4.11-4.05 (m, 2H), 3.96 (s, 3H), 3.49-3.43 (m, 2H), 2.59 (s, 3H), 2.49 (s, 3H); MS (ES+) m/z 374.1 (M+1).
Sources & evidence
- ORD record
- ord-bb41bb38275a4cc3b384803e0083ff2a
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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