[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:20]([O-])=O)=[C:10]([NH:12][C:13](=[O:19])[N:14]([CH3:18])[CH2:15][CH2:16][CH3:17])[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[Zn]>[NH2:20][C:9]1[CH:8]=[CH:7][C:6]([C:1]2[CH2:5][CH2:4][CH2:3][CH:2]=2)=[CH:11][C:10]=1[NH:12][C:13](=[O:19])[N:14]([CH3:18])[CH2:15][CH2:16][CH3:17]To a stirred solution 3-(5-(cyclopent-1-en-1-yl)-2-nitrophenyl)-1-methyl-1-propylurea (0.17 g, 0.56 mmol, 1.0 equiv.) in MeOH were added Zn (0.18 g, 2.80 mmol, 5.0 equiv.) and HCOONH4 (0.28 d, 4.48 mmol, 8.0 equiv.) at room temperature. The reaction was stirred for 2 h then filtered through celite. The organic layer was concentrated and the crude residue was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2) to afford 3-(2-amino-5-(cyclopent-1-en-1-yl)phenyl)-1-methyl-1-propylurea (0.12 g, 78% yield). ESI+ MS: m/z 274 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 7.61 (s, 1H), 7.08 (d, J=1.5 Hz, 1H), 7.01 (dd, J=8.0, 1.5 Hz, 1H), 6.66 (d, J=8.0 Hz, 1H), 5.94-8.90 (m, 1H), 4.77 (s, 2H), 3.24 (t, J=7.5 Hz, 2H), 2.92 (s, 3H), 2.58-2.52 (m, 2H), 2.46-2.40 (m, 2H), 1.95-1.86 (m, 2H), 1.52 (sext, J=7.5 Hz, 2H), 0.86 (t, J=7.5 Hz, 3H).
Loading…
