Reaktion #1932900

Reaktionsgleichung

1-(piperidin-4-ylmethyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

4-maleimidobutyric acid

1-hydroxybenzotriazole

→

1-(4-{4-[(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-1-yl}-4-oxobutyl)-1H-pyrrole-2,5-dione

Ausbeute 37.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 1 hour
2. 2
   workup.STIRRINGthe mixture was stirred an additional hour
3. 3
   ExtraktionThe aqueous layer was extracted with ethyl acetate (2×75 mL) and dichloromethane (2×75 mL)
4. 4
   Waschenwashed with water (2×100 mL) and brine
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by HPFC on silica gel (gradient elution with 2-20% CMA in chloroform)

Vorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.266 g, 1.39 mmol) was added to a mixture of 4-maleimidobutyric acid (0.254 g, 1.39 mmol) and 1-hydroxybenzotriazole (0.187 g, 1.39 mmol) in DMF (13 mL). The mixture was stirred for 1 hour, then 1-(piperidin-4-ylmethyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (0.450 g, 1.39 mmol) was added. The mixture was stirred for 1 hour, then water (60 mL) was added, and the mixture was stirred an additional hour. The aqueous layer was extracted with ethyl acetate (2×75 mL) and dichloromethane (2×75 mL). The organic layers were combined, washed with water (2×100 mL) and brine, and then concentrated under reduced pressure. The resulting residue was purified by HPFC on silica gel (gradient elution with 2-20% CMA in chloroform) to provide 0.251 g of 1-(4-{4-[(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-1-yl}-4-oxobutyl)-1H-pyrrole-2,5-dione as a yellow foam. Anal. Calcd for C27H32N6O3.0.75H2O: C, 64.36; H, 6.68; N, 16.53. Found: C, 64.59; H, 6.73; N, 16.74.

Quelle