3-Pyridinemethanamine → 5-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

HRID 560811Notes

Reaction equation

HRID 560811 reaction equation
F[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:17][C:16]([C:18]([OH:20])=O)=[C:15]([CH3:21])[CH:14]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.C(N1C(=O)N(C2SC(C(O)=O)=C(C)C=2)C=N1)C1C=CC=CC=1.[NH2:46][CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1>>[CH2:6]([N:7]1[C:11](=[O:12])[N:10]([C:13]2[S:17][C:16]([C:18]([NH:46][CH2:47][C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)=[O:20])=[C:15]([CH3:21])[CH:14]=2)[CH:9]=[N:8]1)[C:5]1[CH:4]=[CH:3][CH:2]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 594811755-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acidHCID 594811895-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 594813085-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamideYield 89%

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 5-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 89% yield: mp 180-181° C.; 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.54 (s, 1H), 7.73 (s, 1H), 7.71 (d, J=8.1 Hz, 1H), 7.43-7.25 (m, 6H), 6.88 (s, 1H), 6.48 (t, J=5.6 Hz, 1H), 5.00 (s, 2H), 4.61 (d, J=5.6 Hz, 2H), 2.52 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 150.4, 149.2, 149.0, 140.8, 135.6, 135.3, 134.5, 132.2, 128.8, 128.4, 128.2, 125.1, 120.0, 49.8, 41.4, 16.0: MS (ES+) m/z 406.2 (M+1).

Sources & evidence

ORD record
ord-c0db5e333d4c46a3bf14309af2f1a2c4
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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