Reaktion #40509
ord-86d07ec1acad4deaa6bd9c111eed8bdd
Reaktionsgleichung
Edukte
Reagenzien
Reaktionsbedingungen
Aufarbeitung
- 1workup.ADDITIONThe mixture was poured into a separatory funnel
- 2ExtraktionThe mixture was extracted with EtOAc (2×20 mL)
- 3Waschenthe combined organic layers were washed with brine
- 4TrocknenThe organic layer was dried over magnesium sulfate
- 5Filtrationfiltered
- 6Einengenconcentrated
- 7Sonstigeto yield a yellow-brown oil which
- 8Sonstigewas purified via column chromatography
- 9workup.DISSOLUTIONThe resulting yellow solid was dissolved in methanol (2 mL)
- 10workup.ADDITIONHCl in Et2O (2M, 2 mL) was added
- 11workup.STIRRINGThe mixture was stirred for 5 minutes
- 12Einengenconcentrated
Vorschrift
To a solution of 4-(2-amino-butyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-β-carbolin-8-yl)-amide (100 mg, 0.233 mmol) in pyridine (4 mL) was added 2-methyl-nicotinic acid (38.4 mg, 0.280 mmol) and EDCI (71.5 mg, 0.373 mmol). The solution was stirred overnight at room temperature, then diluted with water (5 mL). The mixture was poured into a separatory funnel and diluted further with water (20 mL). The mixture was extracted with EtOAc (2×20 mL), then the combined organic layers were washed with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield a yellow-brown oil which was purified via column chromatography. The resulting yellow solid was dissolved in methanol (2 mL) and HCl in Et2O (2M, 2 mL) was added. The mixture was stirred for 5 minutes, then concentrated to yield 103 mg of 6,6-dimethyl-4-{2-[(2-methyl-pyridine-3-carbonyl)-amino]-butyl}-morpholine-3-carboxylic acid (6-chloro-9H-β-carbolin-8-yl)-amide (71% yield).