4-methoxy-3-(2-morpholin-4-ylethoxy)benzaldehyde → HCID 178437859, Verbindung

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Reaktionsgleichung

[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[O:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CCOC(C)=O>[CH:1]1([N:6]2[C:10]3=[N:11][C:23]([C:22]4[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[C:20]([O:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)[CH:21]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.25 g, 5.63 mmol), 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde (1.64 g), and xylenes (12 ml) was heated at 160° C. overnight. Additional aldehyde (0.5 g) was added and the mixture was refluxed until complete, then cooled to room temperature. The solvent was stripped, the residue was slurried with EtOAc and the product was collected by filtration and combined with the product from a similar experimental run. The combined product was recrystallized from CH3CN to afford 1-cyclopentyl-3-ethyl-6-[4-methoxy-3-[2-(4-morpholinyl)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 205-206° C.

Aufarbeitung

temperaturethe mixture was refluxed until complete,
temperaturethen cooled to room temperature
filtrationthe product was collected by filtration
customThe combined product was recrystallized from CH3CN

Quellen und Nachweise

ORD-Eintrag: ord-577ffdea0cc147b0b7baecb1645c690e
Quelldatensatz: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05958929

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