Trifluoroacetic acid → 2,6-difluoro-N-(4-(prop-1-en-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

HRID 1255131Notes

Reaction equation

HRID 1255131 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:10]([C:12](O)([CH3:14])[CH3:13])[N:11]=1)=[O:5].C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)=[C:10]([C:12]([CH3:14])=[CH2:13])[N:11]=1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 247655782,6-Difluoro-N-(4-(2-hydroxypropan-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

Product 1

HCID 247655792,6-difluoro-N-(4-(prop-1-en-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of Compound 68 (22 mg, 0.05 mmol) in 5 mL of toluene was added dropwise of 0.2 mL of TFA. The mixture was heated to reflux for 30 minutes. After cooled down to room temperature, the reaction was concentrated. The residue was purified by column chromatography on silica gel (10-20% EtOAc in hexanes) to give Compound 68a (20 mg, 95%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. concentrationthe reaction was concentrated
  4. customThe residue was purified by column chromatography on silica gel (10-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c80198d2b8ca4d768c80c2c0f98cf101
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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