[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]N1C(=O)CCC1=O)=O.[CH3:16][O:17][C:18]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:19]=1[CH2:20][NH:21][CH2:22][C:23]#[CH:24].C([O-])(O)=O.[Na+]>CC#N.O>[CH3:16][O:17][C:18]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:19]=1[CH2:20][N:21]([CH2:22][C:23]#[CH:24])[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8]
A solution of 1-[(1H-pyrrol-2-ylcarbonyl)oxy]pyrrolidine-2,5-dione (1 eq), N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine (1.05 eq) and NaHCO3 (1 eq) in a mixture of CH3CN and H2O (20:1) was heated at reflux for 12 hrs and then the MeCN was removed under reduced pressure. The resulting residue was partitioned between DCM and sat. aq. NaHCO3 solution. The organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and the resulting brown oil was purified by Biotage system eluting with EtOAc/petrol ether to obtain the desired amide. MS (ES) C17H18N2O3 requires: 298, found: 299 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ: 11.56 (1H, br. S), 7.40 (1H, d, J=8.3 Hz), 6.91 (1H, s), 6.60 (1H, d, J=2.1 Hz), 6.52 (1H, dd, J=8.3, 2.1 Hz), 6.48-6.35 (1H, m), 6.09 (1H, s), 4.68 (2H, s), 4.22 (2H, s), 3.80 (3H, s), 3.76 (3H, s), 3.24 (1H, s).
Loading…
