Methylamine → 2-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-2H-[1,2,4]triazole-3-carboxylic acid methylamide

HRID 455037Notes

Reaction equation

HRID 455037 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][N:19]3[C:23]([C:24](OC)=[O:25])=[N:22][CH:21]=[N:20]3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH3:28][NH2:29]>CO>[CH3:28][NH:29][C:24]([C:23]1[N:19]([CH2:18][C:8]2[N:6]3[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]3=[N:10][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:20]=[CH:21][N:22]=1)=[O:25]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 67027486Methyl 1-((6-methyl-2-p-tolylimidazo[1,2-a]pyridin-3-yl)methyl)-1H-1,2,4-triazole-5-carboxylate

Product 1

HCID 670274852-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-2H-[1,2,4]triazole-3-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-((6-methyl-2-p-tolylimidazo[1,2-a]pyridin-3-yl)methyl)-1H-1,2,4-triazole-5-carboxylate was treated with excess methylamine in methanol in a sealed tube at 80° C. for several hours until the reaction was completed as judged by TLC or LC analysis. Solvent was evaporated and the crude product was purified by chromatography (SiO2 column, eluted with 50% acetone). m/e+ 361 for C20H21N6O [M+H]+; 1H-NMR (300 MHz, CDCl3) δ 8.13 (d, J=0.6 Hz, 1H), 7.87 (d, J=8.1 Hz, 2H), 7.65 (s, 1H), 7.57 (d, J=9.3 Hz, 1H), 7.27 (d, J=8.1 Hz, 2H), 7.08 (dd, J=1.2, 9.3 Hz, 1H), 6.32 (s, 2H), 3.06 (d, J=5.1 Hz, 3H), 2.50 (bs, 1H), 2.41 (s, 3H), 2.31 (s, 3H) ppm; 13C-NMR (75 MHz, CDCl3, δ) 158.440, 150.38, 146.788, 146.587, 138.174, 131.289, 129.586, 129.413, 128.819, 128.612, 122.655, 122.094, 117.100, 113.447, 44.395, 26.393, 21.605, 18.714 ppm.

Workup

  1. customSolvent was evaporated
  2. customthe crude product was purified by chromatography (SiO2 column, eluted with 50% acetone)

Sources & evidence

ORD record
ord-7234dcbf1a294744a8beac593776c067
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

Loading…