Reaktion #956096

Reaktionsgleichung

3-(quinoxalin-2-yl)propanoic acid

HOBt

EDCI

quinoline-5,6-diamine

→

N-(6-aminoquinolin-5-yl)-3-(quinoxalin-2-yl)propanamide

N-(5-Aminoquinolin-6-yl)-3-(quinoxalin-2-yl)propanamide

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred for 3 hours
2. 2
   WaschenThe mixture was washed with water (10 mL)
3. 3
   Extraktionextracted with DCM (30 mL×3)
4. 4
   TrocknenThe combined organic layers were dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto afford a yellow mixture which
8. 8
   Sonstigewas purified by reverse phase chromatography

Vorschrift

To a solution of 3-(quinoxalin-2-yl)propanoic acid (550 mg, 2.7 mmol) in DCM (30 mL) was added HOBt (550 mg, 4 mmol) and EDCI (780 mg, 4 mmol). After stirring for 30 minutes, quinoline-5,6-diamine (430 mg, 2.7 mmol) was added and the reaction was stirred for 3 hours. The mixture was washed with water (10 mL) and extracted with DCM (30 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford a yellow mixture which was purified by reverse phase chromatography. N-(5-Aminoquinolin-6-yl)-3-(quinoxalin-2-yl)propanamide (180 mg) and N-(6-aminoquinolin-5-yl)-3-(quinoxalin-2-yl)propanamide (80 mg) were isolated. MS (ESI) m/z 343 (M+H+).

Quelle