Maleic Acid → N1-{4-[4-amino-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-4-(trifluoromethyl)benzamide, trimaleate salt

Participants

Reaction Steps

N1-{4-[4-Amino-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-4-(trifluoromethyl)benzamide (78 mg, 0.128 mmol) was dissolved in hot ethyl acetate (10 mL) and maleic acid (45 mg, 0.387 mmol) in hot ethyl acetate (1 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solvent was removed and ethyl acetate was added and the solid was collected by filtration to give N1-{4-[4-amino-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-4-(trifluoromethyl)benzamide, trimaleate salt (115 mg, 94%). 1H NMR (DMSO-d6) δ 1.87 (m, 2H), 2.24 (m, 4H), 2.79 (s, 3H), 3.01-3.57 (bm, 11H), 3.93 (s, 3H), 5.09 (m, 1H), 6.12 (s, 6H), 7.32 (m, 2H), 7.93 (d, J=8.37 Hz, 2H), 8.04 (d, J=8.11 Hz, 1H), 8.16 (d, J=8.18 Hz, 2H), 8.29 (s, 1H), 9.84 (s, 1H). LCMS (Micromass-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4.5 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, PH 4.5), 3.5 mL/min.): MH+=609.4, Rt=2.50 min.

Provenance & Evidence