Trifluoroacetic acid → HCID 58392302, compound

HRID 561632Notes

Reaction equation

HRID 561632 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[F:24])(O)[CH3:12])[CH2:10][CH2:9]1.[CH3:25][S:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:36]=1[NH:35][CH:34]=[CH:33]2>ClCCl>[CH:8]1([C:11]([C:33]2[C:32]3[C:36](=[C:28]([CH2:27][S:26][CH3:25])[CH:29]=[CH:30][CH:31]=3)[NH:35][CH:34]=2)([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[F:24])[CH3:12])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 58392457HCID 58392457, compound

Product 1

HCID 58392302HCID 58392302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.02 ml (0.24 mmol) of trifluoroacetic acid was added to 50.0 mg (0.20 mmol) of the compound from Example 136A and 35.7 mg (0.20 mmol) of the compound from Example 8A in 4 ml of dichloromethane, and the mixture was stirred at RT overnight. 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 10.0 mg (12% 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-99ae3eb188e14263b82f7727125852cc
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…