Reaktion #2446038

Reaktionsgleichung

compound

Ammonium 6-oxo-3-(phenylamino)-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

1,1′-carbonyldiimidazole

Ammonium hydroxide

→

title compound

Ausbeute 33.4%

6-Oxo-3-(Phenylamino)-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

Ausbeute 33.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction stirred for 72 h
2. 2
   SonstigeSolvents were removed in vacuo
3. 3
   Sonstigethe crude residue purified by chromatography on silica (0-15% THF in DCM)

Vorschrift

To a suspension of the compound of Example 14 (370 mg, 1.02 mmol) in anhydrous DMF (5 mL) was added 1,1′-carbonyldiimidazole (182 mg, 1.12 mmol) and the reaction stirred at r.t. under nitrogen for 20 mins. Ammonium hydroxide (2 mL of 28% NH3 in water) was added and the reaction stirred for 72 h. Solvents were removed in vacuo and the crude residue purified by chromatography on silica (0-15% THF in DCM) to give the title compound as a white solid (123 mg). δH (DMSO-d6) 8.74 (1H, s), 7.67-7.34 (3H, m), 7.33-7.27 (2H, m), 7.22-7.00 (5H, m), 6.82-6.71 (3H, m), 6.21 (1H, d, J 9.7 Hz). LCMS (ES+) RT 3.04 minutes, 362 (M+H)+.

Quelle