Isoxazole, 4-(chloromethyl)-3,5-dimethyl- → 2-(1-((3,5-dimethylisoxazol-4-yl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560747Notes

Reaction equation

HRID 560747 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Cl[CH2:14][C:15]1[C:16]([CH3:21])=[N:17][O:18][C:19]=1[CH3:20].[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]>>[CH3:21][C:16]1[C:15]([CH2:14][N:41]2[C:42](=[O:43])[N:38]([C:25]3[S:26][C:27]([C:28]([NH:30][CH2:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)=[O:29])=[C:23]([CH3:22])[N:24]=3)[CH:39]=[N:40]2)=[C:19]([CH3:20])[O:18][N:17]=1

Participants

4

Reactant 3

HCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 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 594813002-(1-((3,5-dimethylisoxazol-4-yl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 45%

Procedure

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 4-(chloromethyl)-3,5-dimethylisoxazole 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 45% yield: mp 233-234° C. (ethyl acetate/hexane): 1H NMR (300 MHz, CDCl3) δ 8.74 (br s, 1H), 8.60 (br s, 1H), 8.22 (s, 1H), 7.87-7.80 (m, 1H), 7.52-7.31 (m, 1H), 6.51 (t, J=5.8 Hz, 1H), 4.74 (s, 2H), 4.64 (d, J=5.8 Hz, 2H), 2.64 (s, 3H), 2.48 (s, 3H), 2.32 (s, 3H); MS (ES+) m/z 426.1 (M+1).

Sources & evidence

ORD record
ord-4f8c7a9faa0e4b6d8f480189de9ead8a
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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