Trifluoroacetic acid → {4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid

HRID 1767871Notes

Reaction equation

HRID 1767871 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][C:19]3[S:23][C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[N:21][C:20]=3[CH3:34])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:34][C:20]1[N:21]=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:29]=2)[S:23][C:19]=1[CH2:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[CH:9][N:8]2[CH2:7][C:6]([OH:35])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11699008{4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11362826{4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acidYield 11.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester (50 mg, 99 μmol) in dichloromethane (4 ml) was added trifluoroacetic acid (1 ml). The reaction mixture was stirred for 2 h at ambient temperature. The solvent was removed under reduced pressure and the residue purified by preparative HPLC to give 5 mg (11 μmol, 11%) of the title compound as light yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-c39f0cb972c8461ba5ee630c81e06e88
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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