Water → [1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide

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Reaktionsgleichung

[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][CH:9]=[O:10].[C:11](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.O>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:7][N:6]1[C:2]([NH:1][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:3]([NH:8][CH:9]=[O:10])[CH:4]=[N:5]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

The crude product of N-(5-amino-1-methyl-1H-pyrazol-4-yl)formamide (13.33 g) was dissolved in N,N-dimethylformamide (130 ml). To the solution were added trityl chloride (29.2 g), triethylamine (66.3 ml) and 4-dimethylaminopyridine (465 mg), and the mixture was stirred at 60° C. for 5 hours. To the reaction mixture was added water, and the whole mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a white solid. The solid was triturated with ethyl acetate/diisopropyl ether (1:1) to give N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide (19.18 g). The NMR spectrum of this compound indicates the existence of its rotamer.

Aufarbeitung

extractionthe whole mixture was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customto give a white solid
customThe solid was triturated with ethyl acetate/diisopropyl ether (1:1)

Quellen und Nachweise

ORD-Eintrag: ord-00042078e6d34b3eb8c53b1975e753ae
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07129232B2

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