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

HRID 560748Notes

Reaction equation

HRID 560748 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Cl.Cl[CH2:15][C:16]1[N:17]=[C:18]([CH3:21])[S:19][CH:20]=1.[CH3:22][C:23]1[N:24]=[C:25]([N:38]2[C:42](=[O:43])[NH:41][N:40]=[CH:39]2)[S:26][C:27]=1[C:28]([NH:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)=[O:29]>>[CH3:22][C:23]1[N:24]=[C:25]([N:38]2[C:42](=[O:43])[N:41]([CH2:15][C:16]3[N:17]=[C:18]([CH3:21])[S:19][CH:20]=3)[N:40]=[CH:39]2)[S:26][C:27]=1[C:28]([NH:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)=[O:29]

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 594812404-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 594812024-methyl-2-(1-((2-methylthiazol-4-yl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 34%

Procedure

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 4-(chloromethyl)-2-methylthiazole hydrochloride 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 34% yield: 1H NMR (300 MHz, CDCl3) δ 8.57 (br s, 1H), 8.46 (br s, 1H), 8.26 (s, 1H), 7.72-7.63 (m, 1H), 7.30-7.17 (m, 1H), 7.05 (s, 1H), 6.83 (t, J=5.8 Hz, 1H), 5.06 (s, 2H), 4.58 (d, J=5.8 Hz, 2H), 2.64 (s, 3H), 2.61 (s, 3H); MS (ES+) m/z 428.1 (M+1).

Sources & evidence

ORD record
ord-e6814122e8f54093bac2378a781237ab
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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