3-Pyridinemethanamine → 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[C:14](=[O:15])[N:13](CC3C=CC(C(F)(F)F)=CC=3)[N:12]=[CH:11]2)[S:5][C:6]=1[C:7]([OH:9])=O.CC1N=C(N2C(=O)NN=C2)SC=1C(O)=O.[N:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][NH2:49])[CH:43]=1>>[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[C:14](=[O:15])[NH:13][N:12]=[CH:11]2)[S:5][C:6]=1[C:7]([NH:49][CH2:48][C:44]1[CH:43]=[N:42][CH:47]=[CH:46][CH:45]=1)=[O:9]Participants
4
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-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 65% yield: mp 278-279° C. (ethyl acetate/hexane); 1H NMR (300 MHz, DMSO-d6) δ 8.87 (t, J=5.8 Hz, 1H), 8.61 (s, 1H), 8.53-8.48 (m, 1H), 8.45-8.39 (m, 1H), 7.72-7.65 (m, 1H), 7.37-7.29 (m, 1H), 4.39 (d, J=5.8 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.6, 151.9, 151.8, 149.4, 148.6, 135.7, 135.2, 133.4, 123.9, 122.3, 41.0, 17.4; MS (ES+) m/z 317.2 (M+1).
Sources & evidence
- ORD record
- ord-a788e57565fc4a34922276bd34a7791e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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