Methylamine → HCID 53482872, compound

Participants

Reaction Steps

To a solution of (S)-2-(1-((3-amino-2-cyanophenyl)amino)ethyl)-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridine-5-carboxylic acid (0.058 g, 0.139 mmol) in DMF (0.93 mL) was added benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (181 mg, 0.348 mmol) followed by DIEA (0.049 mL, 0.278 mmol) and methylamine (2.0M solution in THF, 0.174 mL, 0.348 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 0-8% MeOH in DCM) to afford a light yellow solid. Repurified by MPLC (eluted with a gradient of 0-90% (1:10:90 NH4OH:MeOH:DCM solution) in DCM) to afford 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-3-(5-fluoro-3-pyridinyl)-N-methylimidazo-[1,2-a]pyridine-5-carboxamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (br. s., 3H) 2.28 (d, J=4.70 Hz, 3H) 5.35 (quin, J=6.94 Hz, 1H) 7.00 (dd, J=6.75, 0.88 Hz, 1H) 7.08 (d, J=7.43 Hz, 1H) 7.22 (br. s., 2H) 7.39 (dd, J=9.00, 6.85 Hz, 1H) 7.67 (br. s., 1H) 7.78 (dd, J=9.10, 0.88 Hz, 1H) 7.87 (s, 1H) 8.31 (br. s., 1H) 8.57 (d, J=2.74 Hz, 1H) 8.73 (q, J=4.30 Hz, 1H). LC-MS (ESI) m/z 432.0 [M+H]+.

Provenance & Evidence