HCID 67539498, compound → HCID 67539640, compound

Participants

Reaction Steps

A solution of [3-(4-chlorophenyl)-3-fluoro-4-oxo-4-(4-quinazolin-4-yl-piperazin-1-yl)-butyl]-carbamic acid tert-butyl ester (226 mg, 0.43 mmol) in DCM (2 mL) and 2.0 M HCl in Et2O (1 mL) was stirred for 12 hours. The mixture was concentrated in vacuo and chromatographed (SiO2) using 10% MeOH/DCM followed by 10% (7N NH3 in MeOH)/DCM as eluent. The purified material was dissolved in MeOH followed by the addition of 2.0N HCl in Et2O, and then concentrated in vacuo. The resulting glass was heated at reflux in isopropyl alcohol and concentrated in vacuo. The resulting solid was suspended in acetonitrile and concentrated in vacuo (repeated twice) to give 4-amino-2-(4-chlorophenyl)-2-fluoro-1-(4-quinazolin-4-yl-piperazin-1-yl)-butan-1-one dihydrochloride as a white powder. 1H NMR (DMSO-d6, 400 MHz) δ 8.86 (s, 1H), 8.18 (m, 4H), 8.01 (m, 2H), 7.69 (m, 1H), 7.58 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.6 Hz, 2H), 4.23 (m, 2H), 4.09 (m, 1H), 3.80 (m, 4H), 3.47 (m, 1H), 2.86 (m, 1H), 2.67 (m, 2H), 2.41 (m, 1H). LCMS (APCI+) m/z 428, 430 [M+H]+.

Provenance & Evidence