N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide → 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)-2,3-dihydro-1H-imidazol-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide
Reaction equation
C(NC(C1SC(N2C(O)CN(CC3C=CC(F)=CC=3)C2=O)=NC=1C)=O)C1C=CC=CC=1.O[CH:33]1[N:37]([C:38]2[S:39][C:40]([C:44]([NH:46][CH2:47][C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)=[O:45])=[C:41]([CH3:43])[N:42]=2)[C:36](=[O:54])[N:35]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][CH:57]=2)[CH2:34]1>>[CH3:43][C:41]1[N:42]=[C:38]([N:37]2[CH:33]=[CH:34][N:35]([CH2:55][C:56]3[CH:57]=[CH:58][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:60][CH:61]=3)[C:36]2=[O:54])[S:39][C:40]=1[C:44]([NH:46][CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1)=[O:45]Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in Example 17, making variations as required to replace N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide with 2-(5-hydroxy-2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 81% yield: mp 163-164° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.58-8.48 (m, 2H), 7.71-7.67 (m, 1H), 7.59 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 2H), 7.29-7.21 (m, 3H), 6.29 (d, J=3.3 Hz, 1H), 4.82 (s, 2H), 4.53 (d, J=5.7 Hz, 2H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.2, 153.5, 153.4, 150.5, 149.2, 148.9, 139.5, 135.8, 133.7, 130.8, 128.4, 128.1, 126.0, 122.0, 119.6, 113.1, 107.9, 46.9, 41.5, 17.3; MS (ES+) m/z 474.3 (M+1).
Sources & evidence
- ORD record
- ord-50763ecb77d844688d6f7fa05fc0aec5
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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