2-Chlorobenzylamine → (2-Chloro-benzyl)-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-amine

Participants

Reaction Conditions

Reaction Steps

The mixture of 3-(2-methanesulfonyl-pyrimidin-4-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine (from Example 46 supra) (150 mg, 0.402 mmol) and 2-chlorobenzylamine (228 mg, 1.608 mmol) was heated at 140° C. with stirring for 2 hours. The oil was purified by chromatography (silica gel, 10 g, 200˜300 mesh, eluting with dichloromethane:methanol, 30:1˜10:1) to afford the crude product (90 mg). The crude product 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 (2-chloro-benzyl)-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-amine; hydrochloride. (Yield 25 mg, 14.3%). 1H NMR (300 MHz, CD3OD): δ 8.62 (s, 1H), 8.58 (s, 1H), 8.25 (s, 1H), 7.52-7.38 (m, 4H), 7.23 (brs, 2H), 5.49-5.45 (m, 2H), 4.87 (brs, 2H), 3.56 (brs, 4H), 3.24 (brs, 2H), 2.87 (s, 3H). LC-MS: [M+H]+ 435.

Provenance & Evidence