Maleic Acid → HCID 178488206, Verbindung

HRID 897568

Reaktionsgleichung

Reaktionsgleichung von HRID 897568
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:32]3[CH2:37][CH2:36][C@H:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:34][CH2:33]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:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49]>C(OCC)(=O)C>[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:32]3[CH2:33][CH2:34][C@H:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:36][CH2:37]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

Komponenten

4

Edukt 2

HCID 444266Maleic AcidHCID 178488203HCID 178488203, Verbindung

Produkt 1

HCID 178488206HCID 178488206, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

trans-N2-(4-{4-Amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide (545 mg, 0.917 mmol) was dissolved in hot ethyl acetate (60 mL) and maleic acid (320 mg, 2.75 mmol) in hot ethyl acetate (5 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solid was collected by filtration to trans-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide, dimaleate salt (473 mg). 1H NMR (DMSO-d6) δ 1.60 (m, 2H), 2.06 (m, 6H), 2.68 (s, 3H), 2.83-3.57 (bm, 9H), 3.96 (s, 3H), 4.04 (s, 3H), 4.72 (m, 1H), 6.18 (s, 6H), 7.16 (m, 1H), 7.28-7.36 (m, 4H), 7.59 (d, J=8.44 Hz, 1H), 7.72 (d, J=7.94 Hz, 1H), 8.13 (d, J=8.15, 1H), 8.28 (s, 1H), 9.44 (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+=594.4, Rt=2.24.

Aufarbeitung

  1. filtrationThe solid was collected by filtration to trans-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide, dimaleate salt (473 mg)
  2. waitEluents: 0% B/A to 100% B/A in 4 min. (B

Quellen und Nachweise

ORD-Eintrag
ord-daa212b62124408b9f37f4ddd7e8b047
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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