Triethylamine → Adamantane-1-carboxylic acid (5-chloro-thiazol-2-yl)-amide

HRID 255076

Reaktionsgleichung

[NH2:1][C:2]1[S:3][C:4]([Cl:7])=[CH:5][N:6]=1.[C:8]12([C:18](Cl)=[O:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[Cl:7][C:4]1[S:3][C:2]([NH:1][C:18]([C:8]23[CH2:17][CH:12]4[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]4)[CH2:15]2)[CH2:9]3)=[O:19])=[N:6][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2-amino-5-chlorothiazole (2.00 g, 14.9 mmol), 1-adamantanecarbonyl chloride (3.54 g, 17.8 mmol), 4-dimethylaminopyridine (1.10 g, 0.90 mmol) and triethylamine (4.15 mL, 23.0 mmol) in 80 mL of THF was stirred at 80° C. for 48 hours The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed with brine. The layers were separated and the aqueous phase was extracted twice with 50 mL of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, dichloromethane) afforded 2.27 g of the title compound: MS (DCI/NH3) m/z 297 (M+H)+.

Aufarbeitung

temperaturewas cooled to ambient temperature
washwashed with brine
customThe layers were separated
extractionthe aqueous phase was extracted twice with 50 mL of ethyl acetate
dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (SiO2, dichloromethane)

Quellen und Nachweise

ORD-Eintrag: ord-db9f264b210b4ee888b9dfde0a1eb5e9
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07875639B2

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