Dimethylformamide → HCID 118062072, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Intermediate 302E (26.7 mg, 0.159 mmol) in toluene (3 mL) was added TEA (0.101 mL, 0.723 mmol), DPPA (0.066 mL, 0.289 mmol) and the solution was heated to 85° C. for 1 hr. The reaction mass was cooled to RT and to it was added a solution of Intermediate 156E (40 mg, 0.145 mmol) in DMF (1 mL) and the reaction mixture was stirred at RT for 8 h. It was then concentrated and extracted with ethyl acetate (3×10 mL) The combined organic layer was dried over Na2SO4, filtered and the filtrate concentrated. The crude product was further purified by preparative HPLC to afford Compound 302 as an off-white solid (32 mg, 50%). HPLC retention times 1.41 min. and 1.41 min. (Methods E and L respectively). MS(ES): m/z=441 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71 (t, J=1.76 Hz, 1H), 7.64 (dt, J=6.65, 1.95 Hz, 1H), 7.41-7.47 (m, 2H), 7.37 (s, 2H), 7.19 (br. s., 1H), 4.75 (s, 2H), 4.44-4.61 (m, 2H), 4.15 (t, J=5.52 Hz, 2H), 3.86 (t, J=5.52 Hz, 2H), 2.81 (t, J=12.30 Hz, 4H).

Provenance & Evidence