2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid → N-((1H-pyrazol-3-yl)methyl)-2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamide

HRID 560768Notes

Reaction equation

HRID 560768 reaction equation
CC1N=C(N2C(=O)N(CC3C=CC(C(F)(F)F)=CC=3)N=C2)SC=1C(O)=O.[F:27][C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[C:37](=[O:38])[N:36]([C:39]3[S:40][C:41]([C:45](O)=[O:46])=[C:42]([CH3:44])[N:43]=3)[CH:35]=[N:34]2)=[CH:30][CH:29]=1.[NH:50]1[CH:54]=[CH:53][C:52]([CH2:55][NH2:56])=[N:51]1>>[NH:50]1[CH:54]=[CH:53][C:52]([CH2:55][NH:56][C:45]([C:41]2[S:40][C:39]([N:36]3[C:37](=[O:38])[N:33]([CH2:32][C:31]4[CH:48]=[CH:49][C:28]([F:27])=[CH:29][CH:30]=4)[N:34]=[CH:35]3)=[N:43][C:42]=2[CH3:44])=[O:46])=[N:51]1

Participants

4

Reactant 3

HCID 579198022-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 580316664-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acidHCID 178510230HCID 178510230, compound

Product 1

HCID 178433103N-((1H-pyrazol-3-yl)methyl)-2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamideYield 49%

Procedure

Following the procedure as described in Example 21, making variations as required to replace 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid with 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid to react with (1H-pyrazol-3-yl)methanamine, the title compound was obtained as a white solid in 49% yield: mp 178-179° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.23 (s, 1H), 7.59 (br s, 1H), 7.39-7.30 (m, 2H), 7.06-6.96 (m, 2H), 6.88 (t, J=4.7 Hz, 1H), 6.33 (br s, 1H), 6.05 (br s, 1H), 4.95 (s, 2H), 4.64 (d, J=4.7 Hz, 2H), 2.63 (s, 3H); MS (ES+) m/z 414.2 (M+1).

Sources & evidence

ORD record
ord-d2b4b26a6f594e96bf8db8f6c4db937f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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