Tricalcium Phosphate → 3-methyl-1-(2-phenoxyphenyl)-6-(3-phenyl-1,2,4-oxadiazol-5-yl)-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

Participants

Reaction Steps

A solution of Example 12b (500 μL, 0.005 g, 0.0139 mmol) in N,N-dimethylformamide and a solution of 1,1′-carbonyldiimidazole (500 μL, 0.0113 g, 0.069 mmol) in N,N-dimethylformamide were combined and shaken for 1 hour at ambient temperature. A solution of (Z)—N′-hydroxybenzimidamide (69.4 μL, 0.042 mmol) in N,N-dimethylformamide was added and the resulting mixture was reacted in an Anton Paar Synthos 3000 microwave optimizer at 180° C. for 45 minutes. Upon completion, the crude material was concentrated to dryness and purified by reverse phase HPLC (C8, acetonitrile/water (0.1% ammonium acetate), 25-55%) to yield 0.0027 g (37%) of the title compound as the acetic acid salt. 1H NMR (400 MHz, DMSO-d6/D2O) δ 12.39 (s, 1 H), 10.30 (s, 1 H), 8.09 (m, 2 H), 7.61 (m, 4 H), 7.54 (m, 1 H), 7.41 (m, 1 H), 7.33 (m, 3 H), 7.07 (m, 2 H), 6.95 (d, J=7.93 Hz, 2 H), 2.65 (s, 3 H). MS (ESI+) m/z 461.1 (M+H)+.

Provenance & Evidence