ethyl 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate → 3-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylic acid

HRID 560809Notes

Reaction equation

HRID 560809 reaction equation
FC1C=CC(CN2C(=O)N(C3SC(C(OCC)=O)=C(C)C=3)C=N2)=CC=1.[CH3:26][C:27]1[CH:31]=[C:30]([N:32]2[C:36](=[O:37])[N:35]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([S:45]([CH3:48])(=[O:47])=[O:46])=[CH:41][CH:40]=3)[N:34]=[CH:33]2)[S:29][C:28]=1[C:49]([O:51]CC)=[O:50]>>[CH3:26][C:27]1[CH:31]=[C:30]([N:32]2[C:36](=[O:37])[N:35]([CH2:38][C:39]3[CH:40]=[CH:41][C:42]([S:45]([CH3:48])(=[O:46])=[O:47])=[CH:43][CH:44]=3)[N:34]=[CH:33]2)[S:29][C:28]=1[C:49]([OH:51])=[O:50]

Participants

3

Reactant 2

HCID 58031537ethyl 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylateHCID 58031651ethyl 3-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate

Product 1

HCID 594812443-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylic acidYield 74%

Procedure

Following the procedure as described in Example 30, making variations as required to replace ethyl 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate with ethyl 3-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate, the title compound was obtained as a beige solid in 74% yield: 1H NMR (300 MHz, DMSO-d6) δ 13.02 (br s, 1H), 8.79 (s, 1H), 7.92 (d, J=7.1 Hz, 2H), 7.56 (d, J=7.1 Hz, 2H), 7.29 (s, 1H), 5.11 (s, 2H), 3.20 (s, 3H), 2.47 (s, 3H); MS (ES−) m/z 392.2 (M−1).

Sources & evidence

ORD record
ord-e77f9833885244ef808b3443b0e66327
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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