Maleic Acid → HCID 131725044, compound

Participants

Reaction Steps

N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl)benzamide (380 mg, 0.717 mmol) was dissolved in hot ethyl acetate (70 mL) and maleic acid (167 mg, 1.435 mmol) in hot ethyl acetate (3 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The solid was collected by filtration to give N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl) benzamide, dimaleate salt (489 mg, 90%). 1H NMR (DMSO-d6) δ 2.15 (m, 2H), 2.41 (m, 2H), 3.23 (m, 2H), 3.94 (s, 3H), 5.09 (m, 1H), 6.14 (m, s, 4H), 7.33 (m, 2H), 7.76 (m, 1H), 7.88 (m, 1H), 7.99 (m, 1H), 8.28 (s, 1H), 8.33 (m, 2H), 8.70 (bs, 1H), 9.92 (s, 1H). LCMS (Thermoquest AQA single Quad MS, Finnigan HPLC-Column: Genesis, C18, 3 um, 33×4.6 mm. Eluents: 30% B/A to 95% B/A in 4.5 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 0.8 mL/min.): MH+=530.2, Rt=2.03 min.

Provenance & Evidence