Sodium hydride → (6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester

HRID 876936

Reaktionsgleichung

Reaktionsgleichung von HRID 876936
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:22]1[N:27]=[C:26]([Cl:28])[N:25]=[C:24]2[N:29]([CH3:32])[N:30]=[CH:31][C:23]=12>C1COCC1>[C:1]([O:5][C:6](=[O:18])[N:7]([C:22]1[N:27]=[C:26]([Cl:28])[N:25]=[C:24]2[N:29]([CH3:32])[N:30]=[CH:31][C:23]=12)[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2222474,6-dichloro-1-methyl-1H-pyrazolo(3,4-d)pyrimidineHCID 58345941(4-Methanesulfonyl-phenyl)carbamic acid tert-butyl ester

Produkt 1

HCID 58345942(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To (4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester (280 mg) in dry THF (3 ml) was added sodium hydride (60% wt suspension in mineral oil, 1.4 equiv., 33.3 mg) at 0° C. After the effervescence ceased, added 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine 5 (113 mg) and the reaction mixture was allowed to warm up to room temperature overnight. DCM/brine extraction gave crude (6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester, which was reacted with indazole boronic acid pinacol ester in General Procedure A to give 142 as a beige solid (118 mg). NMR (d6-DMSO): 3.24 (3H, s), 4.15 (3H, s), 7.56 (1H, t), 7.74 (1H, d), 8.01 (2H, d), 8.28 (2H, d), 8.32 (1H, d), 8.41 (1H, s), 8.99 (1H, s), 10.54 (1H, br), 13.25 (1H, br). MS: MH+ 420.13

Aufarbeitung

  1. extractionDCM/brine extraction

Quellen und Nachweise

ORD-Eintrag
ord-365f85b01ae94910b6450b3b6d29e71d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987280B2

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