Trifluoroacetic acid → HCID 58392371, compound

HRID 561655Notes

Reaction equation

HRID 561655 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)O)[CH2:10][CH2:9]1.[CH3:23][S:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2>ClCCl>[CH:8]1([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[C:31]2[C:30]3[C:34](=[C:26]([CH2:25][S:24][CH3:23])[CH:27]=[CH:28][CH:29]=3)[NH:33][CH:32]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5315074HCID 5315074, compoundHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392371HCID 58392371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.76 ml (9.82 mmol) of trifluoroacetic acid was added to 1.77 g (8.19 mmol) of the compound from Example 149A and 1.45 g (8.19 mmol) of the compound from Example 8A in 91 ml of dichloromethane, and the mixture was stirred at RT for 2 h. It was concentrated and the residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 98/2) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 890 mg (29% of theory) of the title compound.

Workup

  1. concentrationIt was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 98/2) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-272df9893f384cd99aaabc5eecb48cf3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…