Reaktion #1783407

Reaktionsgleichung

Diphenyl azidophosphate

4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

triethylamine

→

1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one

Lösungsmittel

tert-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigetert-butanol was removed under reduced pressure
2. 2
   workup.ADDITIONchloroform and water were added
3. 3
   Sonstigethe organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeAfter removal of MgSO4 and solvent
7. 7
   Sonstigethe residue was purified by column chromatography on silica gel with chloroform and methanol (98:2 to 90:10)

Vorschrift

Diphenyl azidophosphate (0.083 mL) was added to 4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (56 mg) and triethylamine (0.075 mL) in tert-butanol (1.5 mL) and the mixture was stirred at 100° C. for 4 hours. tert-butanol was removed under reduced pressure, then chloroform and water were added, and the organic layer was separated, washed with brine, and dried over MgSO4. After removal of MgSO4 and solvent, the residue was purified by column chromatography on silica gel with chloroform and methanol (98:2 to 90:10) to give 1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (53 mg) as a white solid.

Quelle