4-(Chloromethyl)benzonitrile → Methyl 2-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate
Reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([N:38]2[CH2:42][CH2:41][NH:40][C:39]2=[O:43])=[N:35][C:34]=1[CH3:44])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([N:38]2[CH2:42][CH2:41][N:40]([CH2:12][C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([O:17][CH3:18])=[O:16])[C:39]2=[O:43])=[N:35][C:34]=1[CH3:44])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1Participants
4
Procedure
Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with methyl 2-(bromomethyl)benzoate (prepared according to Dvornikovs, V., and Smithrud, D. B., J. Org. Chem., (2002), 67, 2160-2167) to react with N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 52% yield: mp 130-133° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.97-7.94 (m, 1H), 7.51-7.27 (m, 8H), 5.95 (br s, 1H), 4.90 (s, 2H), 4.56 (d, J=5.6 Hz, 2H), 4.10-4.05 (m, 2H), 3.90 (s, 3H), 3.56-3.51 (m, 2H), 2.62 (s, 3H); MS (ES+) m/z 465.2 (M+1).
Sources & evidence
- ORD record
- ord-73672cb1593f44869bfa237af736308a
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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