Dimethylformamide → HCID 67448799, compound

Participants

Reaction Steps

Lithium 2-(4-acetyl-3-aminophenoxy)acetate (215 mg), HBTU (379 mg), and 10 mL DMF were combined in a 20 mL glass vial and the resulting slurry was stirred at ambient temperature for 1 hour at which time the reaction mixture became almost homogeneous. To the vial, then, were added 3′-nitrobenzylamine HCl (192 mg) and DIEA (191 μL), and the reaction was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with EtOAc, washed successively with water, sat aq. NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel flash chromatography (hexanes/EtOAc), affording the title compound as a yellow solid. MS (ESI+): m/z 344.10 (MH+). H-NMR (400 MHz, CDCl3): 2.526 (3H, 3), 4.587 (2H, s), 4.641 (2H, d, J=6.4 Hz), 6.091 (1H, d, J=2.8 Hz), 6.239 (1H, dd, J=2.8 Hz, 8.8 Hz), 6.969 (1H, br.s), 7.511 (1H, t, J=7.6 Hz), 7.624 (1H, d, J=7.6 Hz), 7.678 (1H, d, J=8.8 Hz), 7.849 (1H, m), 8.131 (1H, s), 8.141 (1H, d, J=7.6 hz).

Provenance & Evidence