Cyclopropylamine → HCID 58459113, compound

Participants

Reaction Steps

A solution of DIEA (0.062 mL, 0.356 mmol), cyclopropylamine (0.025 mL, 0.36 mmol), (S)-2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-1-phenyl-1H-benzo[d]imidazole-7-carboxylic acid (0.071 g, 0.18 mmol), and PyBOP (0.185 g, 0.356 mmol) in DMF (1.18 mL) was stirred at rt for 1 h. The solution was loaded directly onto silica gel and purified by MPLC (eluted with 0-8% MeOH in DCM) to afford an off white solid that was repurified by MPLC (eluted with 0-100% (1:10:90 NH4OH:MeOH:DCM) solution in DCM) to afford 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-N-cyclopropyl-3-phenylimidazo[1,2-a]pyridine-5-carboxamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.16-0.25 (m, 2H) 0.37-0.49 (m, 2H) 1.44 (d, J=6.65 Hz, 3H) 2.05 (tq, J=7.25, 3.64 Hz, 1H) 5.29 (quin, J=6.80 Hz, 1H) 6.84 (d, J=7.24 Hz, 1H) 6.94 (d, J=6.85 Hz, 1H) 7.12-7.51 (m, 8H) 7.75 (d, J=9.00 Hz, 1H) 7.95 (s, 1H) 8.67 (d, J=3.52 Hz, 1H). LC-MS (ESI) m/z 439.1 [M+H]+.

Provenance & Evidence