Water → 2-(prop-1-en-2-yl)-3H-imidazo[4,5-c]pyridine-6-carboximidamide

HRID 81251

Reaktionsgleichung

Cl.[NH2:2]O.C(=O)(O)[O-].[Na+].O.[CH2:10]=[C:11]([C:13]1[NH:23][C:16]2[CH:17]=[N:18][C:19]([C:21]#[N:22])=[CH:20][C:15]=2[N:14]=1)[CH3:12]>C(O)C>[CH2:10]=[C:11]([C:13]1[NH:23][C:16]2[CH:17]=[N:18][C:19]([C:21](=[NH:2])[NH2:22])=[CH:20][C:15]=2[N:14]=1)[CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Hydroxylamine hydrochloride (37.7 mg, 0.54 mmol), sodium bicarbonate (68.4 mg, 0.81 mmol), and water (0.54 mL) were combined in a vial and stirred for 15 minutes. This solution was added to a vial containing 4-(5-chloropyridin-3-yl)-3-[(1R or S)-1-(trans-4-methylcyclohexyl)ethyl]-2-(prop-1-en-2-yl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (114 mg, 0.27 mmol) dissolved in ethanol (1.3 mL). The mixture was sealed and heated at 100° C. for 1 hour. The reaction was cooled to room temperature, quenched with water, and extracted with ethyl acetate (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 4-(5-chloropyridin-3-yl)-N-hydroxy-3-[(1R or S)-1-(trans-4-methylcyclohexyl)ethyl]-2-(prop-1-en-2-yl)-3H-imidazo[4,5-c]pyridine-6-carboximidamide. MS ESI calc'd. for C24H29ClN6O [M+H]+ 453. found 453.

Aufarbeitung

additionThis solution was added to
customThe mixture was sealed
temperatureThe reaction was cooled to room temperature
customquenched with water
extractionextracted with ethyl acetate (2×)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-586cbef5314540cb93ce5ff67db20aa2
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846657B2

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