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

HRID 2067387Notes

Reaction equation

HRID 2067387 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:30]2[CH2:34][CH2:33][N:32]([CH2:35][C:36]3[CH:45]=[CH:44][C:39]([C:40]([O:42]C)=[O:41])=[CH:38][CH:37]=3)[C:31]2=[O:46])[S:28][CH:29]=1>>[CH3:24][C:25]1[N:26]=[C:27]([N:30]2[CH2:34][CH2:33][N:32]([CH2:35][C:36]3[CH:45]=[CH:44][C:39]([C:40]([OH:42])=[O:41])=[CH:38][CH:37]=3)[C:31]2=[O:46])[S:28][CH:29]=1

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031576Methyl 4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate

Product 1

HCID 580315034-((3-(4-Methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acidYield 65%

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-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate, the title compound was obtained in 65% yield: mp 222-224° C.; 1H NMR (300 MHz, CDCl3) δ 7.89 (d, J=8.4 Hz, 2H), 7.38 (d, J=8.4 Hz, 2H), 6.65 (s, 1H), 4.52 (s, 2H), 3.98-3.93 (m, 2H), 3.45-3.40 (m, 2H), 2.19 (s, 3H); MS (ES+) m/z 318.2 (M+1).

Sources & evidence

ORD record
ord-7c2dd660f7604b22b2635b3f0f0f8e47
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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