Sodium Iodide → (4-{Ethyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

HRID 1393088Notes

Reaction equation

HRID 1393088 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)[CH3:2].Cl[CH2:18][C:19]1[S:23][C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[N:21][C:20]=1[CH3:34].[Na+].[I-].[H-].[Na+]>CN(C=O)C.CCOCC.O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH2:14][CH3:15])[CH2:18][C:19]2[S:23][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[N:21][C:20]=2[CH3:34])=[CH:9][CH:8]=1)[CH3:2]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 69220443(4-Ethylamino-phenoxy)-acetic acid ethyl ester

Product 1

HCID 69220732(4-{Ethyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl esterYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled and stirred solution of crude (4-ethylamino-phenoxy)-acetic acid ethyl ester (0.243 g, containing 0.214 g, 0.96 mmol), 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.308 g, 1.05 mmol, WO02/28433) and NaI (0.144 g, 0.96 mmol) in DMF (3 ml) was added NaH (55% in oil, 0.063 g, 1.44 mmol). The reaction was stirred at RT for 4 h, water was added and diluted with Et2O and extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, dried (Na2SO4) and evaporated to give 0.32 g (70%) of crude (4-{ethyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester as an orange oil, MS: 479 (MH+).

Workup

  1. extractionextracted with aqueous saturated NaHCO3/Et2O (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-887f9a641f5c4197963924fbc00ef610
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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