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

HRID 2067535Notes

Reaction equation

HRID 2067535 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:51]=[CH:50][C:31]([O:32][CH2:33][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:30][CH:29]=1.[N:52]1[CH:57]=[CH:56][CH:55]=[C:54]([CH2:58][NH2:59])[CH:53]=1>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][CH2:34][N:35]2[C:39](=[O:40])[N:38]([C:41]3[S:42][C:43]([C:47]([NH:59][CH2:58][C:54]4[CH:53]=[N:52][CH:57]=[CH:56][CH:55]=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 580316322-(1-(2-(4-fluorophenoxy)ethyl)-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 acid

Product 1

HCID 250964462-(1-(2-(4-fluorophenoxy)ethyl)-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 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-(2-(4-fluorophenoxy)ethyl)-5-oxo-1H-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 45% yield: mp 154-155° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.58 (br s, 1H), 8.53-8.45 (m, 1H), 8.26 (s, 1H), 7.72-7.65 (m, 1H), 7.30-7.21 (m, 1H), 6.98-6.86 (m, 2H), 6.85-6.75 (m, 2H), 6.61 (t, J=5.8 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 4.28-4.15 (m, 4H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.7, 157.6, 154.2, 153.4, 151.0, 149.3, 149.1, 135.8, 133.6, 131.0, 123.7, 121.6, 116.0, 115.9, 115.8, 65.5, 45.3, 41.6, 17.2; MS (ES+) m/z 455.3 (M+1).

Sources & evidence

ORD record
ord-6e3010f4cd374bcc8594187d37a61251
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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