Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 4-[(3,4-Dimethoxy-phenylamino)-methyl]-N-(3-thiophen-2-yl-phenyl)-benzamide

Participants

Reaction Steps

To a stirred solution of 31 (122 mg, 0.696 mmol), acid 4 (182 mg, 0.633 mmol) and BOP (308 mg, 0.696 mmol) in DMF (4 ml) was added B3N (265 μl, 1.90 mmol). The reaction was stirred 3 h at room temperature under nitrogen, quenched with H2O and evaporated. The residue was extracted with ethyl acetate, washed with saturated solutions of NH4Cl, NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuum to form a material which was purified by flash chromatography (eluent 40% EtOAc in hexane) to give the title compound 32 (70 mg, 25%) as a yellow solid. 1H NMR: (DMSO) δ (ppm): 10.25 (s, 1H), 8.09-8.08 (m, 1H), 7.73 (ddd, J=7.6, 3.7, 3.7 Hz, 1H), 7.54 (dd, J=5.1, 1.0 Hz, 1H), 7.49 (d, J=8.2 Hz, 2H), 7.45 (dd, J=3.7, 1.2 Hz, 1H), 7.42-7.32 (m, 2H), 7.13 (dd, J=5.1, 3.7 Hz, 1H), 6.64 (d, J=8.6 Hz, 1H), 6.31 (d, J=2.5 Hz, 1H), 6.00-5.97 (m, 2H), 4.31 (d, J=6.1 Hz, 2H), 3.65 (s, 3H), 3.59 (s, 3H). MS: (calc), 444.2; (obt.) 445.5 (MH)+.

Provenance & Evidence