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

HRID 897840Notes

Reaction equation

HRID 897840 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)[C:3]=12.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41]>C(OCC)(=O)C>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][N:34]([CH3:35])[CH3:36])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)[C:3]=12

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 22347002N2-(4-{4-amino-1-[2-(dimethylamino)ethyl]-1H-pyrazolo [3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide

Product 1

HCID 86586283N2-(4-{4-amino-1-[2-(dimethylamino)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide monomaleateYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

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.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-a6eee935322e4281aa544f3b73e0d924
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…