Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate → 2-(3-(Cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HRID 560606Notes

Reaction equation

HRID 560606 reaction equation
CC1N=C(N2CCN(C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[CH:24]1([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:37][C:38]([C:42]([O:44]CC)=[O:43])=[C:39]([CH3:41])[N:40]=3)[C:32]2=[O:47])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH:24]1([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:37][C:38]([C:42]([OH:44])=[O:43])=[C:39]([CH3:41])[N:40]=3)[C:32]2=[O:47])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031626Ethyl 2-(3-(cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 580313962-(3-(Cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidYield 86%

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 ethyl 2-(3-(cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained in 86% yield: 1H NMR (300 MHZ, DMSO-d6) δ 4.06-3.82 (m, 2H), 3.52-3.42 (m, 2H), 2.98 (d, J=6.9 Hz, 2H), 2.52 (s, 3H), 1.73-1.52 (m, 6H), 1.27-1.08 (m, 3H), 0.90-0.72 (m, 2H): MS (ES+) 324.2 (M+1).

Sources & evidence

ORD record
ord-896d2f95aa8140e4892463778af9d71e
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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