4-(Chloromethyl)benzonitrile → Ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate
Reaction equation
ClC[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.BrCC1C=CC([C:17]([O:19][CH2:20][CH3:21])=[O:18])=CC=1.[CH2:24]([NH:31][C:32]([C:34]1[S:38][C:37]([N:39]2[CH2:43][CH2:42]N[C:40]2=[O:44])=[N:36][C:35]=1[CH3:45])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([NH:31][C:32]([C:34]1[S:38][C:37]([N:39]2[CH2:43][CH2:42][N:8]([CH2:7][C:6]3[CH:9]=[C:10]([CH:3]=[CH:4][CH:5]=3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:40]2=[O:44])=[N:36][C:35]=1[CH3:45])=[O:33])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1Participants
Procedure
Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with ethyl 4-(bromomethyl)benzoate 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 20% yield: mp 118-120° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.01 (d, J=8.3 Hz, 2H), 7.35-7.27 (m, 7H), 5.88 (t, J=5.5 Hz, 1H), 4.56 (d, J=5.5 Hz, 2H), 4.51 (s, 2H), 4.36 (q, J=7.1 Hz, 2H), 4.10-4.05 (m, 2H), 3.47-3.42 (m, 2H), 2.60 (s, 3H), 1.37 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 166.1, 162.3, 157.1, 155.4, 153.1, 140.5, 137.9, 130.3, 130.1, 128.8, 128.1, 127.8, 127.6, 117.3, 61.1, 47.7, 44.0, 42.0, 41.8, 17.2, 14.3; MS (ES+) m/z 479.4 (M+1).
Sources & evidence
- ORD record
- ord-147324359eee43c186c5732c1a46db9d
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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