Trifluoroacetic acid → HCID 58392321, compound

HRID 561688Notes

Reaction equation

HRID 561688 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19](O)[CH:20]2[CH2:22][CH:21]2[C:23]#[N:24])=[C:15]([O:26][CH3:27])[CH:14]=1.[CH3:28][S:29]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:41]=1[NH:40][CH:39]=[CH:38]2)(=[O:31])=[O:30].[Cl-].[NH4+]>ClCCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:38]2[C:37]3[C:41](=[C:33]([CH2:32][S:29]([CH3:28])(=[O:31])=[O:30])[CH:34]=[CH:35][CH:36]=3)[NH:40][CH:39]=2)[CH:20]2[CH2:22][CH:21]2[C:23]#[N:24])=[C:15]([O:26][CH3:27])[CH:14]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 159675indium(III)chlorideHCID 583921672-[(4-Chloro-2-methoxyphenyl)(hydroxy)methyl]cyclopropanecarbonitrileHCID 583922947-[(Methylsulfonyl)methyl]-1H-indole

Product 1

HCID 58392321HCID 58392321, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

104 mg (0.47 mmol) of indium(III) chloride and 0.05 ml (0.70 mmol) of trifluoroacetic acid were added to 93.0 mg (0.39 mmol) of the compound from Example 163A and 112 mg (0.47 mmol) of the compound from Example 86A with a purity of 88% under argon in 5 ml of 1,2-dichloroethane, and the mixture was heated under reflux for 2 h. Addition of the reaction mixture to saturated aqueous ammonium chloride solution was followed by extraction with dichloromethane, drying over magnesium sulfate, filtration and concentration. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 30.5 mg (18% of theory) of diastereomer 1 and 28.0 mg (17% of theory) of diastereomer 2 of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionwas followed by extraction with dichloromethane
  4. dry with materialdrying over magnesium sulfate, filtration and concentration
  5. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-92302f8117914d13a001a27b8e9464ba
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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