2-Bromoethanol → 2-(1-(2-hydroxyethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Reaktionsgleichung

FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][CH2:15][OH:16].[CH3:17][C:18]1[N:19]=[C:20]([N:33]2[C:37](=[O:38])[NH:36][N:35]=[CH:34]2)[S:21][C:22]=1[C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:24]>>[OH:16][CH2:15][CH2:14][N:36]1[C:37](=[O:38])[N:33]([C:20]2[S:21][C:22]([C:23]([NH:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=[C:18]([CH3:17])[N:19]=2)[CH:34]=[N:35]1

Komponenten

Edukt 3

HCID 108982-Bromoethanol

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

HCID 594812404-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Produkt 1

HCID 250966952-(1-(2-hydroxyethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideAusbeute 76 %

Versuchsvorschrift

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 2-bromoethanol to react with 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 76% yield: mp 201-202° C. (ethyl acetate/hexane); 1H NMR (300 MHz, DMSO-d6) δ 8.87 (t, J=5.8 Hz, 1H), 8.71 (s, 1H), 8.51 (br s, 1H), 8.47-8.39 (m, 1H), 7.73-7.66 (m, 1H), 7.37-7.30 (m, 1H), 4.83 (t, J=5.8 Hz, 1H), 4.40 (d, J=5.8 Hz, 2H), 3.78 (t, J=5.5 Hz, 2H), 3.68-3.58 (m, 2H), 2.53 (s, 3H); MS (ES+) m/z 361.2 (M+1).