Maleic Acid → N2-(4-{4-amino-1-[2-(dimethylamino)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide monomaleate

Participants

Reaction Steps

To a warm solution of N2-(4-{4-amino-1-[2-(dimethylamino)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide (0.009 g, 0.02 mmol) in ethyl acetate (2 mL) was added a solution of maleic acid (0.005 g, 0.04 mmol) in ethyl acetate (1 mL). The reaction mixture was allowed to cool to ambient temperature and the precipitate was collected by filtration and dried in vacuo to afford N2-(4-{4-amino-1-[2-(dimethylamino)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide monomaleate as a white solid (0.005 g, 0.008 mmol): 1H NMR (d6-DMSO, 400 MHz): δH 9.46 (1H, s), 8.32 (1H, s), 8.15 (1H, d, J=8.0 Hz), 7.71 (1H, d, J=7.6 Hz), 7.59 (1H, d, J=8.4 Hz), 7.32-7.35 (4H, m), 7.16 (1H, t, J=7.4 Hz), 6.06 (2H, s), 4.75 (2H, t, J=6.0 Hz), 4.04 (3H, s), 3.96 (3H, s), 3.65 (2H, t, J=5.6 Hz), and 2.88 (6H, s); RP-HPLC (Hypersil C18, 5 μm, 100 Å, 15 cm; 5%-100% acetonitrile-0.1 M ammonium acetate over 15 min, 1 mL/min). Rt 10.08 min. MS: M+ 485.2.

Provenance & Evidence