1-(Bromomethyl)-4-(trifluoromethyl)benzene → 2-(1-(2-(4-chlorophenylamino)-2-oxoethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 2067524Notes

Reaction equation

HRID 2067524 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:16].[CH3:25][C:26]1[N:27]=[C:28]([N:41]2[C:45](=[O:46])[NH:44][N:43]=[CH:42]2)[S:29][C:30]=1[C:31]([NH:33][CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)=[O:32]>>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[CH2:14][N:44]2[C:45](=[O:46])[N:41]([C:28]3[S:29][C:30]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[C:26]([CH3:25])[N:27]=3)[CH:42]=[N:43]2)=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 2193222-Bromo-n-(4-chlorophenyl)acetamideHCID 594812404-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 250969352-(1-(2-(4-chlorophenylamino)-2-oxoethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 25%

Procedure

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 2-bromo-N-(4-chlorophenyl)acetamide 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 25% yield: mp 255-256° C. (ethyl acetate/hexane); 1H NMR (300 MHz, DMSO-d6) δ 10.39 (s, 1H), 8.90 (t, J=5.8 Hz, 1H), 8.79 (s, 1H), 8.52 (br s, 1H), 8.44 (br s, 1H), 7.75-7.65 (m, 1H), 7.61-7.49 (m, 2H), 7.39-7.28 (m, 3H), 4.67 (s, 2H), 4.40 (d, J=5.8 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 484.2 (M+1).

Sources & evidence

ORD record
ord-0dc15444c3d84f5195115407ac49ecd5
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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