Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate → 4-Methyl-2-(2-oxo-3-phenethylimidazolidin-1-yl)thiazole-5-carboxylic acid

HRID 560596Notes

Reaction equation

HRID 560596 reaction equation
CC1N=C(N2CCN(C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[CH3:24][C:25]1[N:26]=[C:27]([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:28][C:29]=1[C:30]([O:32]CC)=[O:31]>>[CH3:24][C:25]1[N:26]=[C:27]([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:28][C:29]=1[C:30]([OH:32])=[O:31]

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031553Ethyl 4-methyl-2-(2-oxo-3-phenethylimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 594812044-Methyl-2-(2-oxo-3-phenethylimidazolidin-1-yl)thiazole-5-carboxylic acidYield 92%

Procedure

Following the procedure as described in Example 5, making variations as required to replace ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate with ethyl 4-methyl-2-(2-oxo-3-phenethylimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 92% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.29-7.14 (m, 5H), 3.92 (t, J=7.2 Hz, 2H), 3.53-3.41 (m, 4H), 2.79 (t, J=7.8 Hz, 2H), 2.46 (s, 3H); MS (ES+) m/z 332.2 (M+1).

Sources & evidence

ORD record
ord-3546576417ba41c38d2065ab1c2c1317
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…