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

HRID 560806Notes

Reaction equation

HRID 560806 reaction equation
F[C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:17][C:16]([C:18]([O:20]CC)=[O:19])=[C:15]([CH3:23])[CH:14]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.C(N1C(=O)N(C2C(C)=C(C([O-])=O)SC=2)C=N1)C1C=CC=CC=1>>[CH2:6]([N:7]1[C:11](=[O:12])[N:10]([C:13]2[S:17][C:16]([C:18]([OH:20])=[O:19])=[C:15]([CH3:23])[CH:14]=2)[CH:9]=[N:8]1)[C:5]1[CH:24]=[CH:25][CH:2]=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 58031537ethyl 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylateHCID 866452921-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl-3-methylthiophene-2-carboxylate

Product 1

HCID 594811755-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acidYield 86%

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 5-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl-3-methylthiophene-2-carboxylate, the title compound was obtained as a colorless solid in 86% yield: NMR (300 MHz, DMSO-d6) δ 12.99 (br s, 1H), 8.75 (s, 1H), 7.40-7.24 (m, 6H), 4.97 (s, 2H), 2.46 (s, 3H); MS (ES−) m/z 314.2 (M−1).

Sources & evidence

ORD record
ord-b829e2dd25414dd3913249166e750431
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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