Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate → 2-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HRID 2067375Notes

Reaction equation

HRID 2067375 reaction equation
CC1N=C(N2CCN(C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[Cl:24][C:25]1[CH:51]=[CH:50][C:28]2[S:29][CH:30]=[C:31]([CH2:32][N:33]3[CH2:37][CH2:36][N:35]([C:38]4[S:39][C:40]([C:44]([O:46]CC)=[O:45])=[C:41]([CH3:43])[N:42]=4)[C:34]3=[O:49])[C:27]=2[CH:26]=1>>[Cl:24][C:25]1[CH:51]=[CH:50][C:28]2[S:29][CH:30]=[C:31]([CH2:32][N:33]3[CH2:37][CH2:36][N:35]([C:38]4[S:39][C:40]([C:44]([OH:46])=[O:45])=[C:41]([CH3:43])[N:42]=4)[C:34]3=[O:49])[C:27]=2[CH:26]=1

Participants

3

Reactant 2

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateHCID 58031618Ethyl 2-(3-((5-chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidYield 59%

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-((5-chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained in 59% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.86 (s, 1H), 8.06 (d, J=6.0 Hz, 1H), 7.98 (d, J=3.0 Hz, 1H), 7.90 (s, 1H), 7.45-7.41 (m, 1H), 4.69 (s, 2H), 4.00 (t, J=6.0 Hz, 2H), 3.48 (t, J=6.0 Hz, 2H), 2.50 (s, 3H); MS (ES+) m/z 408.1 (M+1).

Sources & evidence

ORD record
ord-b8c0380f404d4ee595ac146ed210ced4
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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