Ethyl 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylate → 4-Methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

HRID 554918Notes

Reaction equation

HRID 554918 reaction equation
FC1(F)CC1CN1CCN(C2SC(C(OCC)=O)=C(C)N=2)C1=O.[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][C:43]([F:46])([F:45])[F:44])[C:36]2=[O:47])[S:28][C:29]=1[C:30]([O:32]CC)=[O:31]>>[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][C:43]([F:44])([F:45])[F:46])[C:36]2=[O:47])[S:28][C:29]=1[C:30]([OH:32])=[O:31]

Participants

3

Reactant 2

HCID 57919843Ethyl 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylateHCID 57919981Ethyl 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 579198994-Methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acidYield 87%

Procedure

Following the procedure as described in Preparation 14, making variations as required to replace ethyl 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate with ethyl 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colourless solid in 87% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.8 (s, 1H), 4.02-3.97 (m, 2H), 3.59-3.54 (m, 2H), 3.33-3.29 (m, 2H), 2.50 (s, 3H), 2.35-2.26 (m, 2H), 1.79-1.69 (m 2H); MS (ES+) m/z 338.1 (M+1).

Workup

  1. customas described in Preparation 14

Sources & evidence

ORD record
ord-46d75c21b73645c6ad3d716bda52f290
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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