Pyridine → HCID 49830279, compound

Participants

Reaction Steps

A mixture of Example 49d (100 mg, 0.323 mmol), phosphoryl trichloride (1 ml, 10.92 mmol) and pyridine (0.05 ml, 0.618 mmol) was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo and purified by HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm), eluting with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A) to give the title product (27 mg, 25.5% yield). MS (ESI) m/e 328 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 1.15-1.48 (m, 5H) 1.58-1.69 (m, 1H) 1.73-1.83 (m, J=9.31, 3.51 Hz, 2H) 1.94-2.03 (m, 2H) 3.76-3.90 (m, 1H) 6.93-7.04 (m, 1H) 7.07 (s, 1H) 7.17 (dd, J=7.93, 4.58 Hz, 1H) 8.28 (d, J=3.36 Hz, 1H) 8.34 (s, 1H) 8.79 (d, J=7.63 Hz, 1H) 12.01 (s, 1H).

Provenance & Evidence