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

HRID 560600Notes

Reaction equation

HRID 560600 reaction equation
CC1N=C(N2CCN(C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[F:24][CH:25]([F:51])[O:26][C:27]1[CH:50]=[CH:49][C:30]([CH2:31][N:32]2[CH2:36][CH2:35][N:34]([C:37]3[S:38][C:39]([C:43]([O:45]CC)=[O:44])=[C:40]([CH3:42])[N:41]=3)[C:33]2=[O:48])=[CH:29][CH:28]=1>>[F:51][CH:25]([F:24])[O:26][C:27]1[CH:50]=[CH:49][C:30]([CH2:31][N:32]2[CH2:36][CH2:35][N:34]([C:37]3[S:38][C:39]([C:43]([OH:45])=[O:44])=[C:40]([CH3:42])[N:41]=3)[C:33]2=[O:48])=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031483Ethyl 2-(3-(4-(difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 594812182-(3-(4-(Difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidYield 88%

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-(4-(difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained in 88% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.43-6.94 (m, 5H), 4.39 (s, 2H), 3.97 (t, J=8.1 Hz, 2H), 3.42 (t, J=8.1 Hz, 2H), 2.46 (s, 3H): MS (ES+) m/z 384.2 (M+1).

Sources & evidence

ORD record
ord-ba000c8a6c124210905acd6378d9b200
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…