3-Pyridinemethanamine → 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide

HRID 2067594Notes

Reaction equation

HRID 2067594 reaction equation
NCC1C=NC=CC=1.[CH3:9][N:10]1[CH:14]=[C:13]([CH2:15][NH2:16])[CH:12]=[N:11]1.[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[C:27](=[O:28])[N:26]([C:29]3[S:33][C:32]([C:34](O)=[O:35])=[C:31]([CH3:37])[CH:30]=3)[CH:25]=[N:24]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[C:27](=[O:28])[N:26]([C:29]3[S:33][C:32]([C:34]([NH:16][CH2:15][C:13]4[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=4)=[O:35])=[C:31]([CH3:37])[CH:30]=3)[CH:25]=[N:24]2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 671225(1-methyl-1H-pyrazol-4-yl)methanamineHCID 594811895-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 594811745-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamideYield 80%

Procedure

Following the procedure as described in Example 31, making variations as required to replace 3-(aminomethyl)pyridine with (1-methyl-1H-pyrazol-4-yl)methylamine 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 168-170° C.; 1H NMR (300 MHz, CDCl3) δ 7.71 (s, 1H), 7.44 (s, 1H), 7.39 (s, 1H), 7.40-7.33 (m, 2H), 7.06-6.98 (m, 2H), 6.86 (s, 1H), 6.02 (t, J=5.0 Hz, 1H), 4.95 (s, 2H), 4.41 (d, J=5.0 Hz, 2H), 3.87 (s, 3H), 2.48 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6 (d, JC-F=247.1 Hz), 162.2, 150.4, 140.0, 138.7, 134.3, 132.3, 131.2 (d, JC-F=3.3 Hz), 130.3 (d, JC-F=8.3 Hz), 129.5, 125.9, 120.2, 118.1, 115.7 (d, JC-F=21.7 Hz), 48.9, 38.9, 34.4, 15.9; MS (ES+) m/z 427.1 (M+1).

Sources & evidence

ORD record
ord-fe9fdc887a1b48479bd3dcc8627b30cb
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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