4-Chloromethyl-5-methyl-2-(3-trifluoromethyl-phenyl)-oxazole → 2-(4-(Ethyl((5-methyl-2-(3-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)amino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 854489Notes

Reaction equation

HRID 854489 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1)[CH3:2].Cl[CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[O:25][C:26]=1[CH3:27]>CN(C=O)C>[CH2:1]([N:3]([CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[O:25][C:26]=1[CH3:27])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:19])([C:11]([F:13])([F:14])[F:12])[C:15]([F:16])([F:18])[F:17])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 105884614-Chloromethyl-5-methyl-2-(3-trifluoromethyl-phenyl)-oxazoleHCID 116663972-(4-(Ethylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 115845082-(4-(Ethyl((5-methyl-2-(3-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)amino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.35 mmol) of 2-(4-ethylamino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol and 96 mg (0.35 mmol) of 4-chloromethyl-5-methyl-2-(3-trifluoromethyl-phenyl)-oxazole (example 22.1) in 0.5 mL of DMF was stirred overnight at 80° C. After distribution of the crude mixture between a saturated aqueous solution of NH4Cl and Et2O, the combined organic phases were dried over Na2SO4 and the solvent was evaporated. Column chromatography on silica gel with toluene/EtOAc gave 91 mg (53%) of 2-(4-{ethyl-[5-methyl-2-(3-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-amino}-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, yellow solid, MS: 527 (MH+).

Workup

  1. dry with materialAfter distribution of the crude mixture between a saturated aqueous solution of NH4Cl and Et2O, the combined organic phases were dried over Na2SO4
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a478d39f0c2146819cd40066baa14f2f
Source dataset
uspto-grants-2007_08
Patent number
US07259178B2

Reaction notes

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