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

HRID 560807Notes

Reaction equation

HRID 560807 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)=CC=1.C1(CCN2C(=O)N(C3SC(C(OCC)=O)=C(C)C=3)C=N2)CC1>>[CH:24]1([CH2:5][CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:17][C:16]([C:18]([OH:20])=[O:19])=[C:15]([CH3:23])[CH:14]=3)[CH:9]=[N:8]2)[CH2:25][CH2:2]1

Participants

3

Reactant 2

HCID 58031435ethyl 5-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylateHCID 58031537ethyl 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate

Product 1

HCID 594812505-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acidYield 96%

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-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate, the title compound was obtained as a colorless solid in 96% yield: NMR (300 MHz, DMSO-d6) δ 12.96 (br s, 1H), 8.72 (s, 1H), 7.26 (s, 1H), 3.81 (t, J=6.5 Hz, 2H), 2.46 (s, 3H), 1.62-1.52 (m, 2H), 0.75-0.60 (m, 1H), 0.40-0.32 (m, 2H), 0.05-−0.05 (m, 2H); MS (ES−) 292.3 (M−1).

Sources & evidence

ORD record
ord-b5c6c12ce2f24f10ba3f90adb93daedd
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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