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

HRID 560749Notes

Reaction equation

HRID 560749 reaction equation
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

Participants

4

Reactant 3

HCID 108982-BromoethanolHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 594812404-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

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

Procedure

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).

Sources & evidence

ORD record
ord-ab7eb990140e44e2af34d1d3948caec9
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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