Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate → 2-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HRID 2067495Notes

Reaction equation

HRID 2067495 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:41][C:42]([C:46]([O:48]CC)=[O:47])=[C:43]([CH3:45])[N:44]=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:41][C:42]([C:46]([OH:48])=[O:47])=[C:43]([CH3:45])[N:44]=3)[C:36]2=[O:51])=[CH:52][CH:53]=1

Participants

3

Reactant 2

HCID 57919911Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 58031427Ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidYield 80%

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 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colorless solid in 80% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.39-7.34 (m, 2H), 7.22-7.17 (m, 2H), 4.43 (s, 2H), 4.01-3.98 (m, 2H), 3.48-3.43 (m, 2H), 2.50 (s, 3H); MS (ES+) m/z 336.1 (M+1).

Sources & evidence

ORD record
ord-28e1ed6b1f494ab9a3a2bcec09e06b93
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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