2-(Dimethylamino)ethanol → HCID 57690626, Verbindung

Temperatur

-78 °C

A solution of 2-dimethylaminoethanol (0.072 ml, 0.72 mmol) in hexanes (3 ml) was cooled down to −40° C. A 2.5M solution of nbutyl lithium in tetrahydrofuran (0.574 ml, 1.44 mmol) was added dropwise. The solution was stirred for 20 minutes. A suspension of tert-butyl 4-(isoquinolin-3-yl)piperazine-1-carboxylate (0.75 mg, 0.24 mmol) in hexanes (8 ml) was added and the resulting solution was stirred for 1 hour. The solution was cooled down to −78° C. A solution of 2-fluoro-N-methoxy-N-methylnicotinamide (176.3 mg, 0.96 mmol) in THF (40 ml) was added dropwise. The reaction mixture was warmed up to −50° and stirred for 1 hour, then the mixture was stirred at 0° C. for a further 1 hour. The crude mixture was partitioned between water and ethyl acetate. The organic extract was dried over magnesium sulfate, filtered and concentrated under vacuo. The residue was and purified on silica gel by flash column chromatography to give the title compound as a yellow oil (8 mg, 8% yield).

1. additionwas added
2. stirringthe resulting solution was stirred for 1 hour
3. temperatureThe reaction mixture was warmed up to −50°
4. stirringstirred for 1 hour
5. stirringthe mixture was stirred at 0° C. for a further 1 hour
6. customThe crude mixture was partitioned between water and ethyl acetate
7. extractionThe organic extract
8. dry with materialwas dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under vacuo
11. custompurified on silica gel by flash column chromatography

ORD-Eintrag

ord-7d425bb02f8f425e967bbf68220cfac0

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08188071B2