Maleic Acid → 1-[1-(1-methyl-4-piperidyl)tetrahydro-1H-3-pyrrolyl]-3-(4-phenoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-4-amine, trimaleate salt

HRID 432293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432293
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:22])=[C:16]4[C:15]([C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)=[N:14]3)[CH2:9]2)[CH2:4][CH2:3]1.[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40]>C(OCC)(=O)C>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:22])=[C:16]4[C:15]([C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)=[N:14]3)[CH2:9]2)[CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 444266Maleic AcidHCID 223470641-[1-(1-methyl-4-piperidyl)tetrahydro-1H-3-pyrrolyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 1317242451-[1-(1-methyl-4-piperidyl)tetrahydro-1H-3-pyrrolyl]-3-(4-phenoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-4-amine, trimaleate saltAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

1-[1-(1-Methyl-4-piperidyl)tetrahydro-1H-3-pyrrolyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (148 mg, 0.315 mmol) was dissolved in hot ethyl acetate (20 mL) and maleic acid (110 mg, 0.946 mmol) in hot ethyl acetate (1 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solid was collected by filtration to give 1-[1-(1-methyl-4-piperidyl)tetrahydro-1H-3-pyrrolyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate salt (230 mg, 90%). 1H NMR (DMSO-d6) δ 1.81 (m, 2H), 2.27 (m, 2H), 2.78 (s, 3H), 2.97-3.84 (bm, 1H), 5.63 (m, 1H), 6.12 (s, 6H), 7.17 (m, 5H), 7.45 (m, 2H), 7.68 (m, 2H), 8.29 (s, 1H). LCMS (Micromass-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4.5 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, PH 4.5), 3.5 mL/min.): MH+ =470.4, Rt=2.01.

Aufarbeitung

  1. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a43fc5c89d1f48e49477111f70065828
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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