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

HRID 560715Notes

Reaction equation

HRID 560715 reaction equation
CC1C=C(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)SC=1C(OCC)=O.[CH3:29][C:30]1[N:31]=[C:32]([N:40]2[CH2:44][CH2:43][N:42]([CH2:45][C:46]3[C:47]([CH3:57])=[N:48][O:49][C:50]=3[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:41]2=[O:58])[S:33][C:34]=1[C:35]([O:37]CC)=[O:36]>>[CH3:29][C:30]1[N:31]=[C:32]([N:40]2[CH2:44][CH2:43][N:42]([CH2:45][C:46]3[C:47]([CH3:57])=[N:48][O:49][C:50]=3[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:41]2=[O:58])[S:33][C:34]=1[C:35]([OH:37])=[O:36]

Participants

3

Reactant 2

HCID 58031427Ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylateHCID 58031639Ethyl 4-methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 580315224-Methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylic acidYield 88%

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 4-methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 88% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.64-7.61 (m, 2H), 7.49-7.47 (m, 3H), 4.40 (s, 2H), 3.87-3.82 (m, 2H), 3.28-3.23 (m, 2H), 2.48 (s, 6H); MS (ES+) m/z 399.1 (M+1).

Sources & evidence

ORD record
ord-f1dfd86a5cb446729204a515cfe3d1c6
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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