1-(1,3-Oxazol-4-yl)methanamine--hydrogen chloride (1/1) → HCID 59481254, compound

HRID 2067546Notes

Reaction equation

HRID 2067546 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.Cl.[O:51]1[CH:55]=[C:54]([CH2:56][NH2:57])[N:53]=[CH:52]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:54]4[N:53]=[CH:52][O:51][CH:55]=4)=[O:46])=[C:42]([CH3:44])[N:43]=3)[CH:35]=[N:34]2)=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 457900281-(1,3-Oxazol-4-yl)methanamine--hydrogen chloride (1/1)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 acid

Product 1

HCID 59481254HCID 59481254, compoundYield 51%

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 oxazol-4-ylmethanamine hydrochloride, the title compound was obtained as a white solid in 51% yield: mp 183-184° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.25 (s, 1H), 7.88 (s, 1H), 7.67 (s, 1H), 7.41-7.32 (m, 2H), 7.08-6.97 (m, 2H), 6.31 (t, J=5.3 Hz, 1H), 4.97 (s, 2H), 4.52 (d, J=5.3 Hz, 2H), 2.63 (s, 3H); MS (ES+) m/z 415.2 (M+1).

Sources & evidence

ORD record
ord-abce8885fc4046e78bc8f91f5304f10f
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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