3-Pyridinemethanamine → 4-methyl-N-(pyridin-3-ylmethyl)-2-(1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)thiazole-5-carboxamide
Reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2S[C:15]([C:19](O)=O)=[C:16](C)[N:17]=2)N=N1)C1C=CC=CC=1.[CH3:22][C:23]1[N:24]=[C:25]([C:31]2[N:32]=[N:33][N:34]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[CH:35]=2)[S:26][C:27]=1[C:28](O)=[O:29].N1C=CC=C(CN)C=1>>[CH3:22][C:23]1[N:24]=[C:25]([C:31]2[N:32]=[N:33][N:34]([CH2:36][C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:44])([F:46])[F:45])=[CH:41][CH:42]=3)[CH:35]=2)[S:26][C:27]=1[C:28]([NH:8][CH2:12][C:11]1[CH:13]=[N:17][CH:16]=[CH:15][CH:19]=1)=[O:29]Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in Example 4, making variations as necessary to replace 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid with 4-methyl-2-(1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)thiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 65% yield: mp 204-205° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.94-8.83 (m, 2H), 8.52 (br s, 1H), 8.43 (br s, 1H), 7.78-7.66 (m, 3H), 7.58-7.51 (m, 2H), 7.38-7.29 (m, 1H), 5.77 (s, 2H), 4.45-4.39 (m, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.5, 157.9, 155.0, 149.3, 148.6, 142.3, 140.6, 135.7, 135.2, 129.3, 129.5, 126.3, 126.2, 125.3, 124.1, 123.9, 53.1, 41.1, 17.5; Ms (ES+) m/z 459.3 (M+1).
Sources & evidence
- ORD record
- ord-437860b98c244246b5c5b7eef6ff676b
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258160B2
Reaction notes
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