Reaktion #161711

Reaktionsgleichung

TBTU

6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid

4-nitro-2,3-dihydro-1H-indole

triethylamine

→

1-{1-[6-(4-nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous phase was extracted with DCM (3×20 mL)
2. 2
   SonstigeThe combined organic phases were dried on magnesium sulphate
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated down i
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 3 mL DMF
6. 6
   Filtrationfiltered through a syringe
7. 7
   Filtrationfilter
8. 8
   Sonstigepurified by preparative HPLC

Vorschrift

150 mg (0.470 mmol) TBTU were added to 150 mg (0.44 mmol) 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 75 mg (0.46 mmol) 4-nitro-2,3-dihydro-1H-indole, 100 μL (0.712 mmol) triethylamine in 1.5 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was poured onto 30 mL water. The aqueous phase was extracted with DCM (3×20 mL). The combined organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was dissolved in 3 mL DMF, filtered through a syringe filter and purified by preparative HPLC. The product fractions were combined and lyophilised.

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