[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Cl[CH2:13][C:14](=O)[CH2:15][O:16][C:17](=[O:19])[CH3:18].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:13]=[C:14]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[N:11]=2)=[N:6][CH:7]=1(5-Bromo-pyridine-2-yl)-thiourea (1 mmol) is dissolved in DMF (2 ml) and acetic acid 3-chloro-2-oxo-propyl ester (1 eq.) is added and stirred 2 h at 70° C. After cooling to RT the reaction solution is poured into water and the resulting precipitate is filtered, washed with water and dried 16 h in vacuo at 40° C. “A5” is obtained as colourless powder in a yield of 82%; mp. 200.9-201.6° C.; HPLC (method C): 1.80 min; LC-MS (method A): 1.800 min, 327.95 (M+H+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 11.516 (s, 1H), 8.391 (d, 1H, J=2.4 Hz), 7.892 (dd, 1H, J=8.9 Hz, J=2.4 Hz), 7.020 (d, 1H, J=8.9 Hz), 6.998 (s, 1H), 5.015 (s, 2H), 2.062 (s, 3H).
Wird geladen…