1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-methyl-1-(2-phenoxyphenyl)-6-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

Participants

Reaction Steps

A solution of Example 12b (200 μL, 0.0275 g, 0.076 mmol) in N,N-dimethylformamide/pyridine (1:1 v/v), a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (200 μL, 0.0225 g, 0.145 mmol) in N,N-dimethylformamide/pyridine (1:1 v/v), and a solution of (Z)—N′-hydroxynicotinimidamide (173.0 μL, 0.103 mmol) in 1 mL of N,N-dimethylformamide/pyridine (1:1 v/v) were combined and shaken at ambient temperature overnight. Upon completion, the reaction mixture was concentrated to dryness. The residue was purified by reverse phase HPLC (C8, acetonitrile/water (0.1% ammonium acetate), 45-75%) to give 0.0031 g (9%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) δ 9.24 (dd, J=2.14, 0.61 Hz, 1H), 8.81 (dd, J=4.88, 1.83 Hz, 1 H), 8.45 (ddd, J=8.09, 1.83, 1.68 Hz, 1 H), 7.67 (m, 1 H), 7.64 (dd, J=7.63, 1.83 Hz, 1 H), 7.59 (s, 1 H), 7.44 (m, 1 H), 7.34 (m, 3 H), 7.07 (m, 2 H), 6.95 (m, 2 H), 2.66 (s, 3 H). MS (ESI+) m/z 562.0 (M+H)+.

Provenance & Evidence