Maleic Acid → HCID 178488196, compound
Reaction equation
[C:1]1([C@@H:7]([CH3:43])[CH2:8][NH:9][C:10](=[O:42])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[N:23][C:24]=4[NH2:26])[N:19]([C@H:27]4[CH2:32][CH2:31][C@@H:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[CH2:29][CH2:28]4)[N:18]=3)=[CH:13][C:12]=2[O:40][CH3:41])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48]>C(OCC)(=O)C>[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[C:1]1([C@@H:7]([CH3:43])[CH2:8][NH:9][C:10](=[O:42])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[N:23][C:24]=4[NH2:26])[N:19]([C@H:27]4[CH2:32][CH2:31][C@@H:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[CH2:29][CH2:28]4)[N:18]=3)=[CH:13][C:12]=2[O:40][CH3:41])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
cis-N1-[(2R)-2-phenylpropyl]-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxybenzamide (100 mg, 0.172 mmol) was dissolved in hot ethyl acetate (12 mL) and maleic acid (60 mg, 0.515 mmol) in hot ethyl acetate (3 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solid was collected by filtration to give cis-N1-[(2R)-2-phenylpropyl]-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxybenzamide, dimaleate salt (117 mg, 87%). 1H NMR (DMSO-d6) δ 1.25 (d, J=6.96, 3H), 1.73 (m, 42H), 2.09 (m, 2H), 2.26 (m, 2H), 2.71 (s, 3H), 2.74 (m, 2H), 2.85-3.70 (bm, 7H), 3.89 (s, 3H), 4.85 (m, 1H), 6.14 (s, 4H), 7.20 (m, 3H), 7.31(d, J=4.33, 4H), 8.12 (d, J=8.17 Hz, 1H), 8.24 (s, 1H), 9.20 (s, 1H). LC/MS (Finigan-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 3.0 mL/min.): MH+=583.4 Rt=2.14 min.