Maleic Acid → HCID 178488208, Verbindung

HRID 432276

Reaktionsgleichung

Reaktionsgleichung von HRID 432276
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)[CH2:33][CH2:32]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[NH:21][C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:29][CH3:30])[CH:12]=3)[C:3]=12.[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].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]4)[CH2:33][CH2:32]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[NH:21][C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:29][CH3:30])[CH:12]=3)[C:3]=12

Komponenten

4

Edukt 2

HCID 444266Maleic AcidHCID 178488207HCID 178488207, Verbindung

Produkt 1

HCID 178488208HCID 178488208, VerbindungAusbeute 108,1 %

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)-1H-2-indolecarboxamide (312 mg, 0.539 mmol) was dissolved in hot ethyl acetate (35 mL) and maleic acid (187 mg, 1.614 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 give trans-N2-(4-{4-Amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1H-2-indolecarboxamide, dimaleate salt (473 mg, 95%). 1H NMR (DMSO-d6) δ 1.60 (m, 2H), 2.09 (m, 6H), 2.68 (s, 3H), 2.84-3.19 (bm, 9H), 3.97 (s, 3H), 4.73 (m, 1H), 6.17 (s, 6H), 7.11 (m, 1H), 7.25 (m, 1H), 7.30 (m, 1H), 7.34 (s, 1H), 7.41 (s, 1H), 7.49 (d, J=8.21, 1H), 7.68 (d, J=8.02 Hz, 1H), 8.13 (d, J=8.15 Hz, 1H), 8.26 (s, 1H), 9.44 (s, 1H), 11.38 (s, 1H). LCMS (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+ =580.4, Rt=2.01 min.

Aufarbeitung

  1. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-62ba5c3f2cda41b6aece7e82d6a46416
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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