3-Pyridinemethanamine → 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methyl-N-((2-methylthiazol-4-yl)methyl)thiophene-2-carboxamide
Reaction equation
NCC1C=NC=CC=1.Cl.Cl.[CH3:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17][NH2:18])[N:16]=1.[F:19][C:20]1[CH:41]=[CH:40][C:23]([CH2:24][N:25]2[C:29](=[O:30])[N:28]([C:31]3[S:35][C:34]([C:36](O)=[O:37])=[C:33]([CH3:39])[CH:32]=3)[CH:27]=[N:26]2)=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:41]=[CH:40][C:23]([CH2:24][N:25]2[C:29](=[O:30])[N:28]([C:31]3[S:35][C:34]([C:36]([NH:18][CH2:17][C:15]4[N:16]=[C:12]([CH3:11])[S:13][CH:14]=4)=[O:37])=[C:33]([CH3:39])[CH:32]=3)[CH:27]=[N:26]2)=[CH:22][CH:21]=1Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in Example 31, making variations as required to replace 3-(aminomethyl)pyridine with 1-(2-methyl-1,3-thiazol-4-yl)methylamine dihydrochloride to react with 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid, the title compound was obtained as a colorless solid in 80% yield: mp 148-150° C.; 1H NMR (300 MHz, CDCl3) δ 7.71 (s, 1H), 7.40-7.33 (in, 2H), 7.07-6.99 (in, 2H), 7.03 (s, 1H), 6.89 (s, 1H), 6.50 (t, J=4.9 Hz, 1H), 4.96 (s, 2H), 4.62 (d, J=4.9 Hz, 2H), 2.69 (s, 3H), 2.50 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.7, 162.6 (d, JC-F=247.1 Hz), 162.2, 151.8, 150.4, 140.0, 134.5, 132.4, 131.2 (d, JC-F=3.3 Hz), 130.3 (d, JC-F=8.3 Hz), 126.1, 120.4, 115.7 (d, JC-F=21.7 Hz), 115.0, 48.9, 40.0, 19.1, 16.0; MS (ES+) m/z 444.1 (M+1).
Sources & evidence
- ORD record
- ord-06e7b0df16c9441188d4912ab7c8b90b
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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