3-Pyridinemethanamine → 4-methyl-2-(5-oxo-1-((5-(trifluoromethyl)furan-2-yl)methyl)-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide
Reaction equation
CC1N=C(N2C(=O)N(CC3C=CC(C(F)(F)F)=CC=3)N=C2)SC=1C(O)=O.[CH3:27][C:28]1[N:29]=[C:30]([N:36]2[C:40](=[O:41])[N:39]([CH2:42][C:43]3[O:44][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:46][CH:47]=3)[N:38]=[CH:37]2)[S:31][C:32]=1[C:33]([OH:35])=O.[N:52]1[CH:57]=[CH:56][CH:55]=[C:54]([CH2:58][NH2:59])[CH:53]=1>>[CH3:27][C:28]1[N:29]=[C:30]([N:36]2[C:40](=[O:41])[N:39]([CH2:42][C:43]3[O:44][C:45]([C:48]([F:49])([F:51])[F:50])=[CH:46][CH:47]=3)[N:38]=[CH:37]2)[S:31][C:32]=1[C:33]([NH:59][CH2:58][C:54]1[CH:53]=[N:52][CH:57]=[CH:56][CH:55]=1)=[O:35]Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in Example 21, making variations as required to replace 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid with 4-methyl-2-(5-oxo-1-((5-(trifluoromethyl)furan-2-yl)methyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 57% yield: mp 124-125° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.63 (s, 2H), 8.28 (s, 1H), 7.82-7.75 (m, 1H), 7.36 (s, 1H), 6.77-6.72 (m, 1H), 6.52 (t, J=5.5 Hz, 1H), 6.47-6.42 (m, 1H), 5.04 (s, 2H), 4.66-4.60 (m, 2H), 2.64 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.6, 115.4, 150.9, 150.8, 149.7, 149.3, 149.2, 135.7, 131.4, 123.7, 121.8, 120.5, 116.9, 112.6, 112.5, 110.4, 42.1, 41.6, 17.2; MS (ES+) m/z 465.3 (M+1).
Sources & evidence
- ORD record
- ord-5e7064370e3d49e8a10adb6419b9139f
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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