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

HRID 560709Notes

Reaction equation

HRID 560709 reaction equation
CC1C=C(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)SC=1C(OCC)=O.[F:29][C:30]1[CH:53]=[CH:52][C:33]([CH2:34][N:35]2[CH2:39][CH2:38][N:37]([C:40]3[S:44][C:43]([C:45]([O:47]CC)=[O:46])=[C:42]([CH3:50])[CH:41]=3)[C:36]2=[O:51])=[CH:32][CH:31]=1>>[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:34][N:35]2[CH2:39][CH2:38][N:37]([C:40]3[S:44][C:43]([C:45]([OH:47])=[O:46])=[C:42]([CH3:50])[CH:41]=3)[C:36]2=[O:51])=[CH:52][CH:53]=1

Participants

3

Reactant 2

HCID 58031427Ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylateHCID 58031706Ethyl 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

Product 1

HCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidYield 90%

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-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate, the title compound was obtained as a colorless solid in 90% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.34 (br s, 1H), 7.35 (dd, J=8.6, 5.6 Hz, 2H), 7.19 (t, J=8.6 Hz, 2H), 6.29 (s, 1H), 4.39 (s, 2H), 3.87-3.78 (m, 2 H), 3.48-3.40 (m, 2H), 2.40 (s, 3H); MS (ES+) m/z 335.2 (M+1).

Sources & evidence

ORD record
ord-91f19667eddd4c39ba00428378745d73
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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