Hydrochloric Acid → N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine

Participants

Reaction Steps

To a solution of crude (2-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester (150 mg, 0.280 mmol) in ethanol (5 mL) was added concentrated hydrochloric acid (5 mL) slowly. The reaction mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and then the solid was purified by prep-HPLC. Several drops of concentrated HCl were added to the fractions with product. After sonicating for several minutes, solution was concentrated under reduced pressure to afford N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine; hydrochloride. (Yield 13 mg, 5.57%). 1H NMR (300 MHz, CD3OD): δ 8.81 (brs, 1H), 8.63 (s, 1H), 8.29 (d, 1H, J=6.0 Hz), 7.61-7.52 (m, 3H), 7.46-7.43 (m, 1H), 7.23 (d, 1H, J=5.1 Hz), 5.72 (brs, 1H), 5.47-5.43 (m, 2H), 3.63-3.60 (m, 4H), 3.50-3.48 (m, 2H), 3.29-3.26 (m, 2H), 2.89 (s, 3H). LC-MS: [M+H]+ 436.

Provenance & Evidence