3-Pyridinemethanamine → HCID 59481190, compound

HRID 2067536Notes

Reaction equation

HRID 2067536 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]([OH:47])=O)=[C:42]([CH3:44])[N:43]=3)[CH:35]=[N:34]2)=[CH:30][CH:29]=1.[N:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH2:56][NH2:57])[CH:51]=1>>[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]([NH:57][CH2:56][C:52]4[CH:51]=[N:50][CH:55]=[CH:54][CH:53]=4)=[O:47])=[C:42]([CH3:44])[N:43]=3)[CH:35]=[N:34]2)=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 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 acid

Product 1

HCID 59481190HCID 59481190, compoundYield 68%

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 pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 68% yield: mp 178-179° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.58 (br s, 1H), 8.51 (br s, 1H), 8.27 (s, 1H), 7.72-7.64 (m, 1H), 7.63-7.54 (m, 2H), 7.51-7.42 (m, 2H), 7.33-7.21 (m, 1H), 6.46 (t, J=5.8 Hz, 1H), 5.04 (s, 2H), 4.59 (d, J=5.8 Hz, 2H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 164.3, 161.7, 161.0, 153.4, 150.9, 149.9, 149.3, 149.1, 135.7, 130.9, 130.3, 130.2, 121.6, 115.9, 115.7, 48.9, 41.6, 17.2; MS (ES+) m/z 425.3 (M+1).

Sources & evidence

ORD record
ord-a80e138d45334e7dab7172aa36a7bb71
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…