Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate → 4-((3-(5-Acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

HRID 2067386Notes

Reaction equation

HRID 2067386 reaction equation
CC1N=C(N2CCN(C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[C:24]([C:27]1[S:31][C:30]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:47]=[CH:46][C:41]([C:42]([O:44]C)=[O:43])=[CH:40][CH:39]=3)[C:33]2=[O:48])=[N:29][C:28]=1[CH3:49])(=[O:26])[CH3:25]>>[C:24]([C:27]1[S:31][C:30]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:47]=[CH:46][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=3)[C:33]2=[O:48])=[N:29][C:28]=1[CH3:49])(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031622Methyl 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate

Product 1

HCID 580316644-((3-(5-Acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acidYield 85%

Procedure

Following the procedure as described in Example 6, making variations as required to replace ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate with methyl 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate, the title compound was obtained in 85% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.89 (br s, 1H), 7.90 (d, J=7.5 Hz, 2H), 7.39 (d, J=7.5 Hz, 2H), 4.49 (s, 2H), 4.05-3.90 (m, 2H), 3.52-3.40 (m, 2H), 2.51 (s, 3H), 2.42 (s, 3H); MS (ES+) m/z 360.1 (M+1).

Sources & evidence

ORD record
ord-d5429f496338432886f64e8ec205c264
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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