3-Pyridinemethanamine → 3-methyl-5-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide
Reaction equation
FC1C=CC(CN2C(=O)N(C3SC(C(O)=O)=C(C)C=3)C=N2)=CC=1.[CH3:24][C:25]1[CH:29]=[C:28]([N:30]2[C:34](=[O:35])[N:33]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[N:32]=[CH:31]2)[S:27][C:26]=1[C:47]([OH:49])=O.[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>>[CH3:24][C:25]1[CH:29]=[C:28]([N:30]2[C:34](=[O:35])[N:33]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[N:32]=[CH:31]2)[S:27][C:26]=1[C:47]([NH:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1)=[O:49]Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in Example 31, making variations as required to replace 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid with 3-methyl-5-(5-oxo-1-(4-(trifluoromethyl)-benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 87% yield: mp 176-178° C.; 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.52 (d, J=3.2 Hz, 1H), 7.74 (s, 1H), 7.69 (d, J=7.9 Hz, 1H), 7.60 (d, J=8.1 Hz, 2H), 7.48 (d, J=8.1 Hz, 2H), 7.27 (dd, J=7.9, 3.2 Hz, 1H), 6.88 (s, 1H), 6.45 (t, J=5.5 Hz, 1H), 5.04 (s, 2H), 4.59 (d, J=5.5 Hz, 2H), 2.49 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.5, 150.5, 149.2, 149.0, 140.7, 139.2, 135.6, 134.4, 133.7, 132.6, 130.3, 128.6, 125.8 (q, JC-F=3.8 Hz), 125.5, 123.6, 120.4, 49.1, 41.4, 16.0; MS (ES+) m/z 474.4 (M+1).
Sources & evidence
- ORD record
- ord-735ea28a4b4b4c6a81954c0b5de20e82
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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