Tetrahydrofuran → HCID 118061452, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 307B (29.8 mg, 0.204 mmol) in toluene (2 mL) were added TEA (0.043 mL, 0.305 mmol), DPPA (0.058 mL, 0.254 mmol) and the reaction mixture was heated at 60° C. and stirred for 2 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 (1 mL) and stirred for 12 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by preparative HPLC to afford Compound 307 as an off-white solid (7.55 mg, 17%). HPLC retention time 5.901 min. and 8.366 min. (Methods A and B respectively). MS(ES): m/z=438 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (dd, J=7.0, 2.0 Hz, 1H), 7.68 (ddd, J=8.5, 4.8, 2.3 Hz, 1H), 7.46 (t, J=9.0 Hz, 1H), 7.36 (br. s., 1H), 7.20 (br. s., 1H), 6.88 (s, 1H), 4.71 (s, 2H), 4.12 (t, J=5.3 Hz, 2H), 3.82 (t, J=5.3 Hz, 2H), 2.44 (m, 2H), 2.29-2.17 (m, 2H), 1.46 (d, J=10.8 Hz, 3H), 1.43 (s, 3H).

Provenance & Evidence