3-Pyridinemethanamine → 3-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-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]([S:43]([CH3:46])(=[O:45])=[O: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:38]=[CH:39][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:41][CH:42]=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-(1-(4-(methylsulfonyl)benzyl)-5-oxo-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 61% yield: mp 208-210° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.75 (s, 1H), 8.64 (t, J=5.6 Hz, 1H), 8.54 (s, 1H), 8.46 (d, J=4.4 Hz, 1H), 7.92 (d, J=8.1 Hz, 2H), 7.72 (d, J=7.7 Hz, 1H), 7.56 (d, J=8.1 Hz, 2H), 7.36 (dd, J=7.7, 4.4 Hz, 1H), 7.22 (s, 1H), 5.11 (s, 2H), 4.43 (d, J=5.6 Hz, 2H), 3.21 (s, 3H), 2.43 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.1, 150.0, 148.8, 148.0, 142.0, 140.1, 138.6, 135.0, 134.9, 134.3, 134.1, 128.4, 127.3, 125.6, 123.4, 119.4, 47.9, 43.4, 40.4, 15.6; MS (ES+) m/z 484.4 (M+1).
Sources & evidence
- ORD record
- ord-58d4f02b8dc74b2e9b499b55a0a8d591
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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