3-Pyridinemethanamine → 2-(1-(4-(difluoromethoxy)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560760Notes

Reaction equation

HRID 560760 reaction equation
CC1N=C(N2C(=O)N(CC3C=CC(C(F)(F)F)=CC=3)N=C2)SC=1C(O)=O.[F:27][CH:28]([F:52])[O:29][C:30]1[CH:51]=[CH:50][C:33]([CH2:34][N:35]2[C:39](=[O:40])[N:38]([C:41]3[S:42][C:43]([C:47](O)=[O:48])=[C:44]([CH3:46])[N:45]=3)[CH:37]=[N:36]2)=[CH:32][CH:31]=1.[N:53]1[CH:58]=[CH:57][CH:56]=[C:55]([CH2:59][NH2:60])[CH:54]=1>>[F:52][CH:28]([F:27])[O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:34][N:35]2[C:39](=[O:40])[N:38]([C:41]3[S:42][C:43]([C:47]([NH:60][CH2:59][C:55]4[CH:54]=[N:53][CH:58]=[CH:57][CH:56]=4)=[O:48])=[C:44]([CH3:46])[N:45]=3)[CH:37]=[N:36]2)=[CH:50][CH:51]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580314632-(1-(4-(difluoromethoxy)benzyl)-5-oxo-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 acid

Product 1

HCID 594812962-(1-(4-(difluoromethoxy)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-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-(difluoromethoxy)benzyl)-5-oxo-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 49% yield: mp 151-152° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.55 (br s, 2H), 8.23 (s, 1H), 7.72-7.63 (m, 1H), 7.43-7.30 (m, 2H), 7.29-7.20 (m, 1H), 7.12-7.00 (m, 2H), 6.78 (t, J=5.6 Hz, 1H), 6.46 (t, JH-F=73.8 Hz, 1H), 4.94 (s, 2H), 4.57 (d, J=5.6 Hz, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.7, 153.4, 151.1, 150.9, 149.9, 149.2, 148.9, 135.8, 132.2, 130.0, 129.9, 121.7, 119.9, 119.2, 115.7, 112.3, 48.9, 41.6, 17.2; MS (ES+) m/z 473.3 (M+1).

Sources & evidence

ORD record
ord-b2187ab14fe746efa5ae893bf5231cfb
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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