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

HRID 560812Notes

Reaction equation

HRID 560812 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)=CC=1.C1(CCN2C(=O)N(C3SC(C(O)=O)=C(C)C=3)C=N2)CC1.[NH2:44][CH2:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1>>[CH:22]1([CH2:5][CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:17][C:16]([C:18]([NH:44][CH2:45][C:46]4[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=4)=[O:20])=[C:15]([CH3:21])[CH:14]=3)[CH:9]=[N:8]2)[CH2:23][CH2:2]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 594811895-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acidHCID 594812505-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 250959315-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamideYield 87%

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-(2-cyclopropylethyl)-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 87% yield: mp 148-150° C.; 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.52 (s, 1H), 7.74 (s, 1 H), 7.69 (d, J=7.7 Hz, 1H), 7.27 (s, 1H), 6.87 (s, 1H), 6.44 (t, J=5.7 Hz, 1H), 4.60 (d, J=5.7 Hz, 2H), 3.91 (t, J=7.0 Hz, 2H), 2.50 (s, 3H), 1.70-1.61 (m, 2H), 0.75-0.60 (m, 1 H), 0.47-0.39 (m, 2H), 0.06-−0.02 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.6, 150.5, 149.2, 149.0, 140.8, 135.6, 134.7, 131.6, 125.0, 123.7, 119.9, 46.0, 41.4, 33.4, 16.0, 8.1, 4.0: MS (ES+) m/z 384.4 (M+1).

Sources & evidence

ORD record
ord-b107f01424934fc49dffa437cc5172b6
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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