Cyanoacetic acid → HCID 178511173, compound

Participants

Reaction Steps

To a stirred solution of (R)-1-piperidin-3-yl-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene (72 mg, 297 μmol) in DCM (15 ml) at 0° C., cyanoacetic acid (30.0 mg, 357 μmol), N-hydroxybenzotriazole (56.0 mg, 416 μmol), 4-(dimethylamino)pyridine (58.0 mg, 475 μmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (91.0 mg, 475 μmol) were added. The mixture was then stirred at ambient temperature for 18 hours. The crude reaction mixture was purified by column chromatography on silica gel (gradient: 0 to 6% methanol in DCM) affording 82 mg (92%) of 3-oxo-3-[(R)-3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-piperidin-1-yl]propionitrile. LCMS (Method A, ESI): RT=2.73 min, m+H=310.1; 1H NMR (400 MHz, DMSO-d6) δ: 12.38 (s, 1H), 9.02 (s, 1H), 7.64-7.59 (m, 1H), 7.12 (m, 1H), 5.28-4.96 (m, 1H), 4.81-4.31 (m, 1H), 4.20-3.70 (m, 3H), 3.36-2.96 (m, 2H), 2.44-1.68 (m, 4H).

Provenance & Evidence