Maleic Acid → HCID 86586284, compound

HRID 897842Notes

Reaction equation

HRID 897842 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][N:34]3[CH:38]=[CH:37][N:36]=[CH:35]3)[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:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43]>C(OCC)(=O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][N:34]3[CH:38]=[CH:37][N:36]=[CH:35]3)[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 22347277HCID 22347277, compound

Product 1

HCID 86586284HCID 86586284, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a warm mixture of N2-(4-{4-amino-1-[2-(1H-1-imidazolyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide (0.034 g, 0.067 mmol) in ethyl acetate (2 mL) was added a solution of maleic acid (0.016 g, 0.13 mmol) in ethyl acetate (1 mL); a white precipitate formed immediately. 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-(1H-1-imidazolyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide trimaleate as a yellow solid (0.011 g, 0.011 mmol): 1H NMR (d6-DMSO, 400 MHz): δH 9.44 (1H, s), 8.90 (1H, s), 8.20 (1H, s), 8.12 (1H, d, J=8.0 Hz), 7.71 (1H, d, J=8.0 Hz), 7.58-7.63 (3H, m), 7.32-7.36 (2H, m), 7.24-7.26 (2H, m), 7.16 (1H, t, J=7.6 Hz), 6.18 (6H, s), 4.85 (2H, t, J=6.8 Hz), 4.71 (2H, t, J=5.2 Hz), 4.04 (3H, s), and 4.00 (3H, 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 10.35 min. MS: M+ 508.2.

Workup

  1. customa white precipitate formed immediately
  2. filtrationthe precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cb8d33ee528040afbae9c060a64c5070
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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