Trifluoroacetic acid → HCID 58459334, compound

Participants

Reaction Steps

To a mixture of tert-butyl 1-(1-(pyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl)ethylcarbamate (0.516 g, 1.520 mmol) in DCM (10.14 mL) was added TFA (10.14 mL, 132 mmol) dropwise at rt with stirring. After 50 min, the mixture was concentrated in vacuo and co-evaporated with triethylamine and MeOH. The neutralized crude mixture was purified by chromatography through a Redi-Sep™ pre-packed silica gel column (40 g), eluting with a gradient of 0% to 100% DCM:MeOH:NH4OH (89:9:1) in DCM, to provide 1-(1-(pyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl)ethanamine as brown syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.76 (1H, m), 8.49 (1H, dd, J=4.7, 1.6 Hz), 8.19 (1H, td, J=7.7, 2.0 Hz), 7.79-7.92 (2H, m), 7.63 (1H, ddd, J=7.6, 4.8, 0.9 Hz), 7.32 (1H, dd, J=8.1, 4.8 Hz), 4.47 (1H, q, J=6.7 Hz), 1.45 (3H, d, J=6.8 Hz); LC-MS (ESI) m/z 240.1 [M+H]+.

Provenance & Evidence