[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20]Br)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:22])=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide (1.80 g, 4.54 mmol) in acetone (50 mL) and water (5 mL) was added potassium carbonate (1.50 g, 10.8 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 2 hours. The solvent was removed in vacuo, and the residue was washed with water and t-butyl methyl ether to yield the title compound in 78% yield (1.12 g): mp 222-224° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.60 (t, J=6.0 Hz, 1H), 7.33-7.16 (m, 5H), 4.35 (d, J=6.0 Hz, 2H), 3.97 (t, J=7.2 Hz, 2H), 2.59 (t, J=7.8 Hz, 2H), 2.46 (s, 3H), 2.14-1.94 (m, 2H); MS (ES+) m/z 316.4 (M+1).
Wird geladen…
