2-(Aminomethyl)-5-methylpyrazine → HCID 59481226, compound

HRID 2067548Notes

Reaction equation

HRID 2067548 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.[CH3:50][C:51]1[N:52]=[CH:53][C:54]([CH2:57][NH2:58])=[N:55][CH:56]=1>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:32][N:33]2[C:37](=[O:38])[N:36]([C:39]3[S:40][C:41]([C:45]([NH:58][CH2:57][C:54]4[CH:53]=[N:52][C:51]([CH3:50])=[CH:56][N:55]=4)=[O:46])=[C:42]([CH3:44])[N:43]=3)[CH:35]=[N:34]2)=[CH:48][CH:49]=1

Participants

4

Reactant 3

HCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 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 59481226HCID 59481226, compoundYield 64%

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 (5-methylpyrazin-2-yl)methanamine, the title compound was obtained as a white solid in 64% yield: mp 188-189° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.53 (s, 1H), 8.40 (s, 1H), 8.26 (s, 1H), 7.43-7.33 (m, 2H), 7.10-6.99 (m, 2H), 6.97 (t, J=4.8 Hz, 1H), 4.98 (s, 2H), 4.72 (d, J=4.8 Hz, 2H), 2.66 (s, 3H), 2.58 (s, 3H); MS (ES+) m/z 440.2 (M+1).

Sources & evidence

ORD record
ord-d5718e8cbe374b728d3659df0ae9952a
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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