Tetrahydrofuran → HCID 118062283, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Intermediate 235B (0.082 g, 0.543 mmol) in toluene (0.5 mL) was added TEA (0.076 mL, 0.543 mmol) and DPPA (0.074 mL, 0.339 mmol) and the reaction mass was warmed to 90° C. for 2 h. The reaction mixture was cooled to RT and to it was added a solution of Intermediate 185B (0.04 g, 0.136 mmol) in THF (0.5 mL) and stirred for 12 h. The reaction mixture was quenched with an aqueous solution of 10% NaHCO3 and extracted with ethyl acetate (3×10 mL) The combined organic layer was washed with water, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by preparative HPLC to afford Compound 235 as pale yellow solid (10 mg, 17% yield). HPLC retention times 1.40 and 1.41 min (Method E and L respectively). MS(ES): m/z=442 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (dd, J=7.28, 2.26 Hz, 1H), 7.68 (ddd, J=8.53, 4.77, 2.26 Hz, 1H), 7.43-7.49 (m, 1H), 7.35 (br. s., 1H), 7.30 (s, 1H), 7.20 (br. s., 1H), 6.04-6.34 (m, 1H), 4.75 (s, 2H), 4.14 (t, J=5.27 Hz, 2H), 3.86 (t, J=5.52 Hz, 2H), 2.28-2.35 (m, 3H), 2.09-2.19 (m, 2H), 1.71-1.97 (m, 2H).

Provenance & Evidence