(1-methyl-1H-pyrazol-4-yl)methanamine → HCID 59481311, compound

HRID 560769

Reaction equation

HRID 560769 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][N:51]1[CH:55]=[C:54]([CH2:56][NH2:57])[CH:53]=[N:52]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:57][CH2:56][C:54]4[CH:53]=[N:52][N:51]([CH3:50])[CH: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 671225(1-methyl-1H-pyrazol-4-yl)methanamineHCID 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 59481311HCID 59481311, compoundYield 63%

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 (1-methyl-1H-pyrazol-4-yl)methanamine, the title compound was obtained as a white solid in 63% yield: mp 205-206° C. (ethyl acetate/hexane); NMR (300 MHz, CDCl3) δ 8.24 (s, 1H), 7.45 (s, 1H), 7.41-7.32 (m, 3H), 7.07-6.98 (m, 2H), 5.88 (t, J=5.3 Hz, 1H), 4.97 (s, 2 H), 4.42 (d, J=5.3 Hz, 2H), 3.88 (s, 3H), 2.62 (s, 3H); MS (ES+) m/z 428.2 (M+1).

Sources & evidence

ORD record
ord-d421b78724ec47bd81fb3200553156f9
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Linked notes

Loading…