3-Pyridinemethanamine → HCID 24960066, compound

Participants

Reaction Steps

To a solution of 2-(4-(4-chlorobenzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylic acid (0.05 g, 0.14 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.04 g, 0.20 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.28 mmol) in N,N-dimethylformamide (2 mL) was added 1-hydroxy-benzotriazole (0.05 g, 0.37 mmol). The resulting mixture was stirred at ambient temperature for 15 minutes and 3-(aminomethyl)pyridine (0.02 mL, 0.02 mmol) was added. The reaction mixture was stirred at ambient temperature for 17 hours, diluted with ethyl acetate (30 mL), washed with water and brine. The organic solution was dried over anhydrous sodium sulfate filtered and concentrated in vacuo. The residue was purified by column chromatography to the title compound as a white powder (0.03 g, 48%): mp 215-217° C.: 1H NMR (300 MHz, DMSO-d6) δ 12.31 (br s, 1H), 8.71 (t, J=5.8 Hz, 1H), 8.50 (d, J=1.6 Hz, 1H), 8.42 (dd, J=4.8, 1.6 Hz, 1H), 7.68 (td, J=7.8 Hz, 1.9 Hz, 1H), 7.36-7.19 (m, 5H), 4.38 (d, J=5.8 Hz, 2H), 3.52 (s, 2H), 2.52 (s, 3H), 2.13 (s, 3H); MS (ES+) m/z 454.3 (M+1).

Provenance & Evidence