Methylamine → HCID 67433463, compound

Participants

Reaction Steps

To a solution of DIEA (0.207 mL, 1.18 mmol), PyBOP (0.768 g, 1.475 mmol), and (S)-2-(1-((6-amino-5-cyanopyrimidin-4-yl)amino)ethyl)-3-phenylimidazo-[1,2-a]pyridine-5-carboxylic acid (0.236 g, 0.590 mmol) in DMF (3.93 mL) was added methanamine (2.0M in THF, 0.738 mL, 1.48 mmol). The solution was stirred at rt for 1 h then was loaded onto silica gel and purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford a solid that was repurified by reverse phase analytical HPLC (eluted with a gradient of 10-60% MeCN in water with 0.1% TFA) to afford (S)-2-(14(6-amino-5-cyanopyrimidin-4-yl)amino)-ethyl)-N-methyl-3-phenylimidazo[1,2-a]pyridine-5-carboxamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (d, J=6.65 Hz, 3H) 2.16 (d, J=4.70 Hz, 3H) 5.29 (quin, J=6.90 Hz, 1H) 6.83 (d, J=7.63 Hz, 1H) 6.93 (dd, J=6.85, 1.17 Hz, 1H) 7.18-7.46 (m, 8H) 7.74 (dd, J=9.00, 1.17 Hz, 1H) 7.94 (s, 1H) 8.51 (q, J=4.56 Hz, 1H). LC-MS (ESI) m/z 413.1 [M+H]+.

Provenance & Evidence