Ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate → 2-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylic acid

HRID 560790Notes

Reaction equation

HRID 560790 reaction equation
C(NC(C1SC(N2CCN(CC3C=C(C=CC=3)C(OCC)=O)C2=O)=NC=1C)=O)C1C=CC=CC=1.[F:35][C:36]1[CH:62]=[CH:61][C:39]([CH2:40][N:41]2[CH2:45][CH2:44][N:43]([C:46]3[S:47][C:48]([C:55]([O:57]CC)=[O:56])=[C:49]([C:51]([F:54])([F:53])[F:52])[N:50]=3)[C:42]2=[O:60])=[CH:38][CH:37]=1>>[F:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:40][N:41]2[CH2:45][CH2:44][N:43]([C:46]3[S:47][C:48]([C:55]([OH:57])=[O:56])=[C:49]([C:51]([F:54])([F:52])[F:53])[N:50]=3)[C:42]2=[O:60])=[CH:61][CH:62]=1

Participants

3

Reactant 2

HCID 59481231Ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoateHCID 59481310Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylate

Product 1

HCID 594812062-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylic acidYield 69%

Procedure

Following the procedure as described in Example 25, making variations as required to replace ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate with ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 69% yield: 1H NMR (300 MHz, DMSO-d6) δ 13.74 (br s, 1H), 7.36-7.30 (m, 2H), 7.19-7.13 (m, 2H), 4.41 (s, 2H), 4.02-3.97 (m, 2H), 3.47-3.41 (m, 2H); MS (ES+) m/z 390.1 (M+1).

Sources & evidence

ORD record
ord-63767662b0e34b7d9d69d6e31e9fd8b5
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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