Sodium hydride → HCID 86287822, compound

Participants

Reaction Conditions

Reaction Steps

2-cyclopentylethanol (0.137 g, 1.196 mmol) in tetrahydrofuran (5 mL) was treated with NaH (0.029 g, 1.196 mmol) at ambient temperature, stirred for 5 minutes and treated with the product from Example 17C (0.1 g, 0.299 mmol). The reaction mixture was heated at 60° C. for 12 hours and partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. The resulting residue (0.15 g) was treated with 4 M HCl in dioxane (15 mL), heated at 70° C. for 12 hours, cooled, concentrated and the residue was purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%) to give the title compound (0.05 g, 0.121 mmol, 34.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.96 (d, J=5.0 Hz, 1H), 7.84 (d, J=2.4 Hz, 1H), 7.79 (dd, J=8.7, 2.4 Hz, 1H), 7.57 (s, 1H), 7.33 (d, J=8.7 Hz, 1H), 6.94-6.86 (m, 1H), 6.42 (d, J=6.5 Hz, 1H), 4.31-3.99 (m, 5H), 3.20 (s, 3H), 1.85 (dd, J=14.6, 7.3 Hz, 1H), 1.79-1.63 (m, 4H), 1.62-1.39 (m, 4H), 1.11 (dd, J=12.0, 7.9 Hz, 2H). MS (ESI+) m/z 415.1 (M+H)+.

Provenance & Evidence