Dimethylformamide → HCID 118062828, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 304E (26.3 mg, 0.141 mmol) in toluene (3 mL) was added TEA (0.090 mL, 0.643 mmol) and DPPA (0.059 mL, 0.257 mmol) and the resulting solution was heated at 85° C. for 1 h. The reaction mixture was cooled to RT and to it was added a solution of Intermediate 185B (40 mg, 0.129 mmol) in DMF (1 mL) and stirred at RT for 8 h. It was concentrated and the residue was extracted with ethyl acetate (3×10 mL). The combined organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The crude product was further purified by preparative HPLC to afford Compound 304 as an off-white solid (18 mg, 28%). HPLC retention times 1.57 min. and 1.59 min. (Methods E and L respectively). ES(MS): m/z=478 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90 (d, J=1.5 Hz, 1H), 7.72-7.63 (m, 3H), 7.45-7.21 (m, 2H), 6.47-6.11 (m, 1H), 4.77 (s, 2H), 4.17 (t, J=5.3 Hz, 2H), 3.88 (t, J=5.3 Hz, 2H), 3.06-2.91 (m, 2H), 2.90-2.76 (m, 2H).

Provenance & Evidence