Reaktion #57163

Reaktionsgleichung

dimethylamine

tetrahydrofuran

4-[3-(4-aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine

tetrahydrofuran

→

title compound

Ausbeute 46.0%

N′-{4-[4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-ethyl-1H-pyrazol-3-yl]phenyl}-N,N-dimethylurea

Ausbeute 46.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Einengenthen concentrated under vacuum
3. 3
   SonstigeThe residue which remained was triturated with aqueous sodium hydroxide
4. 4
   Filtrationfiltered
5. 5
   Waschenwashed with cold water
6. 6
   Sonstigedried under vacuum
7. 7
   SonstigePurification by Gilson reverse phase HPLC

Vorschrift

To a stirred solution of 4-[3-(4-aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine (1.0 mmol) in tetrahydrofuran (15 mL) was added p-nitrophenylchloroformate (1.1 mmol). After stirring for 1 h at room temperature a solution of 2.0 M dimethylamine in tetrahydrofuran (14 mmol) was added. The reaction was stirred an additional 1 h at room temperature then concentrated under vacuum. The residue which remained was triturated with aqueous sodium hydroxide, filtered, washed with cold water, and dried under vacuum. Purification by Gilson reverse phase HPLC afforded title compound as an off-white solid (46%). ESMS (M+H)+: 508.4

Quelle