Dimethylformamide → 5,5-Dioxo-2-(pyrid-4-ylethylcarbonylamino)dibenzothiophene

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Reaction Steps

5,5-Dioxo-2-aminodibenzothiophene (J Med Chem, (1994), 37 (13), 2085-9; 115 mg, 0.5 mmol) was dissolved in DMF (2.0 ml) and 3-(pyridin-4-yl)propionic acid (Method 1; 75 mg, 0.5 mmol) was added in one portion followed by EDAC (115 mg, 0.5 mmol) and the resultant mixture was stirred for 72 hours at ambient temperature. It was then poured onto water (50 ml) and extracted with DCM (2×50 ml), dried and evaporated in vacuo. The residue thus obtained was purified by chromatography (Bond Elut column) eluted with 0-0.5% methanol in DCM to give the product as a colourless solid (31.8 mg). NMR 10.52 (brs, 1H), 8.46 (d, 2H), 8.32 (d, 1H), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (d, 1H), 7.76 (d, 1H), 7.70 (t, 1H), 7.64 (t, 1H), 7.26 (d, 2H), 2.93 (t, 2H), 2.75 (t, 2H); m/z 365.

Provenance & Evidence