Carbon Dioxide → 1-[Butyl(methyl)amino]isoquinoline-7-carboxylic acid

HRID 14263

Reaktionsgleichung

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:12]([CH2:14][CH2:15][CH2:16][CH3:17])[CH3:13])=[CH:4][CH:3]=1.C([Li])(CC)C.[C:23](=[O:25])=[O:24].Cl>C(OCC)C>[CH2:14]([N:12]([CH3:13])[C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:23]([OH:25])=[O:24])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[CH2:15][CH2:16][CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

To a −60° C. solution of 7-bromo-N-butyl-N-methylisoquinolin-1-amine (230 mg, 0.78 mmol) in diethyl ether was added sec-butyllithium (1.00 mL of a 1.3 M solution in cyclohexanes, 1.30 mmol). The solution was stirred at −60° C. for 20 min then excess dry ice (CO2) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was then acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The aqueous phase was concentrated under reduced pressure to yield a yellow oil. Purification by flash column chromatography (silica, 50:30:15:5 ethyl acetate/chloroform/methanol/ammonium hydroxide) provided 1-[butyl(methyl)amino]isoquinoline-7-carboxylic acid (90 mg): ESI MS m/z 259 [M+H]+.

Aufarbeitung

temperatureto warm to room temperature
extractionextracted with ethyl acetate
concentrationThe aqueous phase was concentrated under reduced pressure
customto yield a yellow oil
customPurification by flash column chromatography (silica, 50:30:15:5 ethyl acetate/chloroform/methanol/ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag: ord-4d441e06c4224c11bed3d28739cb4527
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07727997B2

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