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

HRID 560711Notes

Reaction equation

HRID 560711 reaction equation
CC1C=C(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)SC=1C(OCC)=O.[CH3:29][C:30]1[CH:34]=[C:33]([N:35]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]2=[O:48])[S:32][C:31]=1[C:49]([O:51]CC)=[O:50]>>[CH3:29][C:30]1[CH:34]=[C:33]([N:35]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]2=[O:48])[S:32][C:31]=1[C:49]([OH:51])=[O:50]

Participants

3

Reactant 2

HCID 58031427Ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylateHCID 58031586Ethyl 3-methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 580314913-Methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)thiophene-2-carboxylic acidYield 78%

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 3-methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as a colorless solid in 78% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.47-7.17 (m, 5H), 6.25 (s, 1H), 3.83-3.74 (m, 2H), 3.56-3.40 (m, 4H), 2.82 (t, J=7.4 Hz, 2H), 2.38 (s, 3H); MS (ES+) m/z 331.3 (M+1).

Sources & evidence

ORD record
ord-dd0a0dabbcb74a3983dffa1e6ec9519e
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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