Tetrahydrofuran → HCID 178505152, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 275a (350 mg, crude, ˜0.414 mmol), methanesulfonyl chloride (95 mg, 0.828 mmol), and Hunig's base (0.217 mL, 1.242 mmol) in THF (4 mL) was stirred at room temperature for 1 day then concentrated in vacuo. To the residue was added dioxane (5 mL) and NaOH (20%, 1 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 provide the title compound (15 mg, 0.036 mmol, 9% yield). MS (ESI) m/e 421 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 1.35-1.51 (m, 4H) 1.98-2.09 (m, 4H) 2.91 (s, 3H) 3.14-3.23 (m, J=8.24 Hz, 1H) 3.71-3.83 (m, J=10.07 Hz, 1H) 6.66-6.76 (m, 1H) 7.04 (d, J=7.63 Hz, 1H) 7.08 (s, 1H) 7.18 (dd, J=7.93, 4.88 Hz, 1H) 8.29 (dd, J=4.58, 1.83 Hz, 1H) 8.34 (s, 1H) 8.78 (d, J=7.94 Hz, 1H).

Provenance & Evidence