Tetrahydrofuran → HCID 178523791, compound

Participants

Reaction Steps

A mixture of Example 42c (120 mg, 0.35 mmol), cyclopropanecarbonyl chloride (36.6 mg, 0.35 mmol), and Hunig's base (0.18 mL, 1.05 mmol) in THF (2.5 mL) was stirred at room temperature for 16 hours. The reaction mixture was concentrated and purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile: 10 mM ammonium acetate in water over 12 minutes at a flow rate of 50 mL/minutes to provide title compound (20 mg, 0.049 mmol, 14% yield). MS (ESI) m/e 411 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 0.56-0.64 (m, 2H) 0.65-0.72 (m, 2H) 1.30-1.47 (m, 4H) 1.49-1.59 (m, 1H) 1.84-1.95 (m, J=6.41 Hz, 2H) 2.00-2.10 (m, 2H) 3.51-3.66 (m, 1H) 3.73-3.86 (m, J=7.63 Hz, 1H) 7.03 (d, J=7.63 Hz, 1H) 7.08 (s, 1H) 7.18 (dd, J=7.93, 4.58 Hz, 1H) 7.54-7.64 (m, 1H) 8.27-8.31 (m, 1H) 8.34 (s, 1H) 8.79 (d, J=7.63 Hz, 1H) 12.00 (s, 1H).

Provenance & Evidence