Trifluoroacetic acid → HCID 58497179, compound

HRID 1254067Notes

Reaction equation

HRID 1254067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[CH:12]=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C1C(=O)N([I:39])C(=O)C1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([I:39])=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 58497212HCID 58497212, compound

Product 1

HCID 58497179HCID 58497179, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of Step 2 product (200 mg, 0.528 mmol) in CH2Cl2 (0.5 ml) was added TFA (3 ml) and NIS (238 mg, 1.06 mmol) at rt, and then reaction mixture was heated to reflux overnight. Reaction mixture was cooled to rt and concentrated. To the residue was added CH2Cl2, quenched with NaHCO3 (aq), washed with aq Na2S2O3, water and brine. Dried over Na2SO4, filtered and concentrated. Separated by prep TLC (hex:EtOAc=1:1) to give 5-[(4-chlorophenyl)sulfanyl]-2-iodo-1-methyl-4-[4-(methylsulfonyl)phenyl]-1H-imidazole as light yellow solid (180 mg). LCMS: [M+1]+=505.0 Human FAAH lysate assay: IC50=15.6 nM.

Workup

  1. customreaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. customReaction mixture
  5. concentrationconcentrated
  6. additionTo the residue was added CH2Cl2
  7. customquenched with NaHCO3 (aq)
  8. washwashed with aq Na2S2O3, water and brine
  9. dry with materialDried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customSeparated by prep TLC (hex:EtOAc=1:1)

Sources & evidence

ORD record
ord-3fbbdcff14954a268d636c1346ed90e1
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

Loading…