3-Pyridinemethanamine → 4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide
Reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=3)[C:33]2=[O:49])[S:27][C:28]=1[C:29]([OH:31])=O.[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>>[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][C:45]([F:46])([F:47])[F:48])=[CH:42][CH:43]=3)[C:33]2=[O:49])[S:27][C:28]=1[C:29]([NH:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1)=[O:31]Participants
Reactant 3
Product 1
Procedure
Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine in place of benzylamine, the title compound was obtained as a white powder in 77% yield: mp 165-166° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.46 (d, J=4.5 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H), 7.29-7.14 (m, 5H), 6.46 (t, J=5.4 Hz, 1H), 4.56 (d, J=5.4 Hz, 2H), 4.43 (s, 2H), 4.04 (t, J=8.1 Hz, 2H), 3.43 (t, J=8.1 Hz, 2H), 2.56 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.2, 155.4, 153.5, 149.0, 148.0, 135.8, 134.3, 129.6, 118.6, 117.0, 47.2, 42.0, 41.7, 41.3, 17.2; MS (ES+) m/z 492.3 (M+1).
Sources & evidence
- ORD record
- ord-5df71660627f4dfeb27b7ccc8a6f4269
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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