Water → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-N4-[(1R)-1-(2-pyridinyl)ethyl]-3,4-quinolinediamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a suspension of 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N—((R)-1-(pyridin-2-yl)ethyl)quinolin-4-amine (Intermediate 24) (1.05 g, 2.503 mmol) in EtOH (20 mL) was added tin(II) chloride (1.66 g, 8.76 mmol) and the mixture stirred at 40° C. for 2.5 h. The reaction mixture was basified to pH 12 using 2M aq. sodium hydroxide solution. Water (30 mL) was added and the aqueous suspension extracted with DCM (3×30 mL). The organic layers were combined, dried by passing through a hydrophobic frit and concentrated to dryness under a stream of nitrogen. The resulting residue was purified by chromatography (100 g column, 2M methanolic ammonia gradient) to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4—((R)-1-(pyridin-2-yl)ethyl)quinoline-3,4-diamine (543 mg, 1.39 mmol, 56% yield) as a dark brown gum.

Herkunft & Nachweise