Ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylate → 5-(3-Benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

HRID 560708Notes

Reaction equation

HRID 560708 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16](C(F)(F)F)=[CH:15][CH:14]=3)[C:8]2=[O:23])[S:4][C:3]=1[C:24]([O:26]CC)=[O:25].C(N1CCN(C2SC(C(OCC)=O)=C(C)C=2)C1=O)C1C=CC=CC=1>>[CH2:12]([N:9]1[CH2:10][CH2:11][N:7]([C:5]2[S:4][C:3]([C:24]([OH:26])=[O:25])=[C:2]([CH3:1])[CH:6]=2)[C:8]1=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 58031427Ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylateHCID 58031603Ethyl 5-(3-benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

Product 1

HCID 580315465-(3-Benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidYield 91%

Procedure

Following the procedure as described in Example 14, making variations as required to replace ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylate with ethyl 5-(3-benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate, the title compound was obtained as a colorless solid in 91% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.36 (br s, 1H), 7.41-7.26 (m, 5H), 6.29 (s, 1H), 4.40 (s, 2H), 3.87-3.80 (m, 2H), 3.48-3.41 (m, 2H), 2.40 (s, 3H); MS (ES+) m/z 317.2 (M+1).

Sources & evidence

ORD record
ord-66acd1b45a45428ba58bd3bf139bed7c
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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