3-Pentanamine → Methyl [4-bromo-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate
Reaction equation
[Br:1][C:2]1[C:3]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[S:5][CH:6]=1.[NH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:13])=[CH:14][CH:15]=2)[S:5][CH:6]=1Participants
4
Procedure
4-(4-Bromo-3-methoxycarbonylmethyl-thiophen-2-yl)-benzoic acid (0.303 g, 0.85 mmol) was dissolved in DMF (2 mL) and carbonyldiimidizole (0.172 g, 1.06 mmol) was added. The solution was stirred at RT for thirty minutes and 3-aminopentane (0.222 g, 2.55 mmol) was added. Stirring was continued for 3 h and the solvent was removed. The mixture was partitioned between EtOAc and H2O. The EtOAc was dried (MgSO4) and the solvent was removed to yield methyl [4-bromo-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate (0.248 g) as a white solid. mp 97-98° C.; 1H NMR (500 MHz, DMSO-d6) δ: 0.87 (t, 6H, J=7.3 Hz), 1.49 (m, 2H), 1.54 (m, 2H), 3.65 (s, 3H), 3.71 (s, 2H), 3.80 (m, 1H), 7.51 (d, 1H, J=8.5 Hz), 7.85 (s, 1H), 7.95 (d, 2H, J=8.5 Hz), 8.12 (d, 1H, J=8.7 Hz). MS (ES) m/z 424.0 ([M+H]+). MS (ES) m/z 456.0 ([M+CH3OH+H]+). MS (ES) m/z 847.0 ([2M+H]+). Anal. Calcd for C19H22BrNO3S: C, 53.78; H, 5.23; N, 3.30. Found: C, 53.65; H, 4.77; N, 3.52.