Tetrahydrofuran → HCID 118061610, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 314F (36.2 mg, 0.153 mmol) in toluene (1 mL) was added TEA (0.071 mL, 0.509 mmol), DPPA (0.044 mL, 0.204 mmol) and the reaction mixture was heated to 85° C. and stirred for 1 h. The reaction mixture was cooled to RT and to it was added a solution of Intermediate 185B (30 mg, 0.102 mmol) in THF (0.5 mL) and stirred at RT for 12 h. The reaction mixture was diluted with EtOAc (10 mL), washed successively with water, a 10% aq. solution of NaHCO3 and brine, then dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC to afford Compound 314 as an off-white solid (0.017 g, 32%). HPLC retention times 1.604 min. and 1.605 min. (Methods E and L respectively). MS(ES): m/z=529.2 [M+H]+; 1H NMR: (400 MHz, DMSO-d6) δ ppm 7.92 (s, 1H), 7.86-7.77 (m, 3H), 7.67 (ddd, J=8.7, 4.9, 2.0 Hz, 1H), 7.64-7.58 (m, 2H), 7.50-7.41 (m, 1H), 7.36 (br. s., 1H), 7.18 (br. s., 1H), 4.73 (s, 2H), 4.14 (t, J=5.3 Hz, 2H), 3.84 (t, J=5.3 Hz, 2H), 3.17 (t, J=12.3 Hz, 4H).

Provenance & Evidence