2-Chlorobenzylamine → (2-Chloro-benzyl)-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl}-pyridin-2-yl]-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(6-bromo-pyridin-2-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine (from Example 39 supra) (0.187 g, 0.5 mmol), 2-chloro-benzylamine (71 mg, 0.5 mmol), Pd2(dba)3 (30 mg), Davephos (40 mg), NaOtBu (70 mg, 0.73 mmol) and dioxane (20 mL) in a sealed tube was bubbled with N2 for several minutes and then heated under N2 at 100° C. for 15 hours. The solution was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The obtained crude product was purified by preparative-HPLC. The obtained product was dissolved in ethanol and then concentrated HCl (1 mL) was added and stirred for 1 h. The mixture was concentrated under reduced pressure. The resulting solid was suspended in dichloromethane and concentrated to give (2-chloro-benzyl)-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl}-pyridin-2-yl]-amine; hydrochloride. (Yield 47 mg). 1HNMR (300 MHz, CD3OD): δ 8.39 (d, 1H, J=5.4 Hz), 8.17 (s, 1H), 7.73 (t, 1H, J=7.8 Hz), 7.40-7.36 (m, 2H), 7.22-7.09 (m, 4H), 6.87 (d, 1H, J=8.4 Hz), 5.43 (brs, 2H), 4.64 (s, 2H), 3.86-3.66 (m, 4H), 3.41-3.37 (m, 2H), 2.91 (s, 3H). LC-MS: [M+H]+ 435.

Provenance & Evidence