4-Hydroxy-2-methylacetophenone → 4-[4-(4-Acetyl-3-methyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1931672

Reaktionsgleichung

Reaktionsgleichung von HRID 1931672
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[C:27]([CH3:34])[CH:26]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[C:27]([CH3:34])[CH:26]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 701334-Hydroxy-2-methylacetophenoneHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Produkt 1

HCID 579650064-[4-(4-Acetyl-3-methyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-[4-(4-Acetyl-3-methyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared according to General Procedure B by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 4′-hydroxy-2′-methylacetophenone (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA) in dimethylformamide. 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 1.97-2.06 (m, 4H), 2.33 (s, 3H), 2.67 (s, 3H), 2.94-3.04 (m, 2H), 4.04-4.10 (m, 2H), 4.98-5.04 (m, 1H), 7.29-7.31 (m, 2H), 7.96-7.98 (m, 1H), 8.29 (s, 1H), 8.55 (s, 1H). Mass spectrum MH+=452.

Quellen und Nachweise

ORD-Eintrag
ord-26664ff485cd477d841281081bf4b462
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188098B2

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