3-Pyridinemethanamine → 4-methyl-2-(5-oxo-1-(4,4,4-trifluorobutyl)-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][CH2:43][CH2:44][C:45]([F:48])([F:47])[F:46])[N:38]=[CH:37]2)[S:31][C:32]=1[C:33]([OH:35])=O.[N:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH2:55][NH2:56])[CH:50]=1>>[CH3:27][C:28]1[N:29]=[C:30]([N:36]2[C:40](=[O:41])[N:39]([CH2:42][CH2:43][CH2:44][C:45]([F:48])([F:47])[F:46])[N:38]=[CH:37]2)[S:31][C:32]=1[C:33]([NH:56][CH2:55][C:51]1[CH:50]=[N:49][CH:54]=[CH:53][CH:52]=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-(4,4,4-trifluorobutyl)-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 35% yield: mp 184-185° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.57 (br s, 1H), 8.49 (br s, 1H), 8.27 (s, 1H), 7.75-7.63 (m, 1H), 7.32-7.20 (m, 1H), 6.62 (t, J=5.6 Hz, 1H), 4.59 (d, J=5.6 Hz, 2H), 3.91 (t, J=6.5 Hz, 2H), 2.63 (s, 3H), 2.28-1.96 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 161.7, 153.4, 150.9, 150.0, 149.2, 149.1, 135.8, 131.0, 128.5, 124.8, 121.2, 44.5, 41.2, 31.3, 30.9, 21.3, 17.2; MS (ES+) m/z 427.3 (M+1).
Sources & evidence
- ORD record
- ord-c1347422c1264886a0c840b200e3bce4
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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