HCID 67539565, compound → HCID 67539710, compound

Participants

Reaction Steps

A solution of (R)-[1-(4-chlorobenzyl)-2-(4-imidazo[1,2-a]pyridin-3-yl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (350 mg, 0.72 mmol) in DCM (3 mL) and 2.0N HCl in Et2O (2 mL) was stirred for 12 hours. The mixture was concentrated in vacuo and the resulting material was chromatographed (SiO2) using 10% MeOH/DCM followed by 10% (7N NH3 in MeOH)/DCM as eluent. This material was dissolved in MeOH followed by the addition of 2.0N HCl in Et2O, and then concentrated in vacuo. The resulting gum was tripped from isopropyl alcohol, and then from acetonitrile to give 2-(R)-amino-3-(4-chlorophenyl)-1-(4-imidazo[1,2-a]pyridin-3-yl-piperazin-1-yl)-propan-1-one dihydrochloride as a white solid (100 mg). 1H NMR (DMSO-d6, 400 MHz) δ 8.66 (d, J=6.8 Hz, 1H), 8.49 (bs, 3H), 7.89 (m, 3H), 7.45 (m, 1H), 7.38 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 2H), 4.69 (bs, 1H), 3.49 (m, 6H), 3.08 (m, 1H), 2.94 (m, 3H), 2.85 (m, 1H). LCMS (APCI+) m/z 384, 386 [m+H]+.

Provenance & Evidence