Trifluoroacetic acid → HCID 67538941, compound

Participants

Reaction Steps

Trifluoroacetic acid (4 mL) was added to a stirred solution of {1-(4-chlorobenzyl)-2-oxo-2-[4-(6-phenyl-quinazolin-4-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (30 mg) in DCM (10 mL) at room temperature. The solution was stirred at room temperature for 4 hours, quenched with aqueous NaOH (1N, 10 mL), diluted with EtOAc (100 mL) and washed with aqueous NaOH (2×50 mL.) The organic phase was dried over Na2SO4 and concentrated in vacuo to give 2-amino-3-(4-chlorophenyl)-1-[4-(6-phenyl-quinazolin-4-yl)-piperazin-1-yl]-propan-1-one as a colorless oil (23 mg.) 1H NMR (CDCl3, 400 MHz) δ 8.77 (1H, s), 8.02-8.00 (2H, m), 7.98 (1H, s), 7.64 (2H, d, J7.4 Hz), 7.53 (2H, t, J7.7 Hz), 7.44 (1H, t, J7.3 Hz), 7.30 (2H, d, J8.6 Hz), 7.17 (2H, d, J8.6 Hz), 3.98 (1H, t, J7.3 Hz), 3.87-3.60 (6H, m), 3.42-3.34 (2H, m), 2.97 (1H, dd, J7.4 and 13.3 Hz), 2.84 (1H, dd, J7.0 and 13.7 Hz.) The oil was taken up into THF (10 mL) and treated with HCl (1.0M in Et2O, 10 mL) and concentrated in vacuo to give the bis hydrochloride salt of 2-amino-3-(4-chlorophenyl)-1-[4-(6-phenyl-quinazolin-4-yl)-piperazin-1-yl]-propan-1-one as a solid (21 mg).

Provenance & Evidence