Trifluoroacetic acid → HCID 58392258, compound

HRID 561653Notes

Reaction equation

HRID 561653 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])O)[CH2:10][CH2:9]1.[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2>ClCCl>[CH:8]1([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:29]2[C:28]3[C:32](=[C:24]([CH2:23][S:22][CH3:21])[CH:25]=[CH:26][CH:27]=3)[NH:31][CH:30]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 58392304HCID 58392304, compound

Product 1

HCID 58392258HCID 58392258, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 ml (2.76 mmol) of trifluoroacetic acid was added to 500 mg (2.30 mmol) of the compound from Example 147A and 408 mg (2.30 mmol) of the compound from Example 8A in 32 ml of dichloromethane, and the mixture was stirred at RT for 30 min. It was concentrated and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 342 mg (35% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationIt was concentrated
  2. 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-a4a7ea6b12e24c84a49643dec1186d66
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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