Reaktion #162231

Reaktionsgleichung

5-fluoro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

6-aminobicyclo-[2.2.1]heptane-2-carboxylic acid

72h

6-aminobicyclo[2.2.1]heptane-2-carboxylic acid

diisopropylethylamine

trifluoroacetic acid

LiOH

→

desired product

6-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)bicyclo[2.2.1]heptane-2-carboxylic acid

Lösungsmittel

THF

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated for another 7 hours
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe resulting filtrate was purified by preparatory HPLC chromatography

Vorschrift

To a solution of 5-fluoro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine (0.187 g, 0.417 mmol) and 6-aminobicyclo-[2.2.1]heptane-2-carboxylic acid, 72h, (0.080 g, 0.417 mmol) in THF (3 mL) was added diisopropylethylamine (0.291 mL, 1.670 mmol). The reaction mixture was heated at 80° C. overnight. Aqueous LiOH (3 mL of 2M solution, 6.000 mmol) was added and the mixture was heated for another 7 hours. The mixture was diluted with MeOH, neutralized with trifluoroacetic acid, filtered and the resulting filtrate was purified by preparatory HPLC chromatography to afford 50 mg of desired product.

Quelle