Cyclopropanecarbonyl chloride → HCID 50940100, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of Example 270a (350 mg, crude, ˜0.414 mmol) and cyclopropanecarbonyl chloride (43.3 mg, 0.414 mmol), Hunig's base (0.217 mL, 1.242 mmol) in THF (4 ml) was stirred at room temperature for 2 hours and then concentrated in vacuo. To the residue was added dioxane (5 mL) and NaOH (20%, 0.8 mL) and heated at 90° C. for 3 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 give the title compound (13 mg, 7.6% yield). MS (ESI) m/e 411 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 0.54-0.63 (m, 2H) 0.63-0.72 (m, 2H) 1.09-1.58 (m, 5H) 1.73-1.88 (m, 2H) 1.97 (s, 1H) 2.18 (s, 1H) 3.68-3.78 (m, 1H) 3.79-3.92 (m, J=7.93 Hz, 1H) 7.04-7.13 (m, 2H) 7.19 (dd, J=7.93, 4.58 Hz, 1H) 7.57-7.69 (m, 1H) 8.27 (dd, J=4.73, 1.37 Hz, 1H) 8.34 (s, 1H) 8.75 (d, J=7.93 Hz, 1H) 12.00 (s, 1H).

Provenance & Evidence