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

HRID 2056035Notizen

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Reaktionsgleichung von HRID 2056035
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][NH:34][CH2:35][CH2:36][OH:37])[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:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42]>C(OCC)(=O)C>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][NH:34][CH2:35][CH2:36][OH:37])[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

Komponenten

4

Edukt 2

HCID 444266Maleic AcidHCID 22347107N2-[4-(4-amino-1-{2-[(2-hydroxyethyl)amino]ethyl}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-1-methyl-1H-2-indolecarboxamide

Produkt 1

HCID 86586282N2-[4-(4-amino-1-{2-[(2-hydroxyethyl)amino]ethyl}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-1-methyl-1H-2-indolecarboxamide monomaleateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a warm solution of N2-[4-(4-amino-1-{2-[(2-hydroxyethyl)amino]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 (0.5 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-[(2-hydroxyethyl)amino]ethyl}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-1-methyl-1H-2-indolecarboxamide monomaleate as a white solid (0.009 g, 0.014 mmol): 1H NMR (d6-DMSO, 400 MHz): δH 9.45 (1H, s), 8.69-8.74 (2H, bs), 8.31 (1H, s), 8.14 (1H, d, J=8.0 Hz), 7.71 (1H, d, J=8.0 Hz), 7.59 (1H, d, J=8.4 Hz), 7.32-7.36 (4H, m), 7.15 (1H, t, J=7.4 Hz), 6.07 (2H, s), 5.28 (1H, t, J=4.2 Hz), 4.71 (2H, t, J=5.8 Hz), 4.04 (3H, s), 3.96 (3H, s), 3.65-3.67 (2H, m), 3.50-3.60 (2H, m), and 3.10-3.20 (2H, m); 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 9.97 min.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-59db6929cae54fa58da9cc4a14826e57
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332497B2

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