5-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrile → 5-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzamide

HRID 1627254Notes

Reaction equation

HRID 1627254 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([S:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=3)[C:31]#[N:32])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=[O:36].OS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:15]([S:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=3)[C:31]([NH2:32])=[O:36])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 667401155-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrileHCID 86586073TFA sulfuric acid

Product 1

HCID 667402815-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzamideYield 77%

Procedure

A solution of 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrile (270 mg, 0.527 mmol) in TFA/H2SO4 (6 mL, 4:1, v/v) was heated at 65° C. for 8 h. The reaction mixture was cooled to room temperature, and the residue was partitioned into DCM and water. The separated organic layer was washed with satd NaHCO3, dried over MgSO4, filtered through Celite™, and concentrated. Purification by flash chromatography (DCM/EtOAc, 1:1) gave the title product (217 mg, 77%) as a white foam. 1H NMR (CDCl3, 400 MHz): δ 1.47 (s, 6H) 4.13 (s, 2H), 6.04 (br s, 1H), 6.36 (m, 2H), 6.65 (br s, 1H), 6.81 (m, 3H), 6.96 (s, 1H), 7.06 (m, 1H), 7.27 (m, 2H), 7.40 (m, 1H), 7.91 (m, 1H); MS (EI) m/z 532 (MH+).

Workup

  1. customthe residue was partitioned into DCM and water
  2. washThe separated organic layer was washed with satd NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through Celite™
  5. concentrationconcentrated
  6. customPurification by flash chromatography (DCM/EtOAc, 1:1)

Sources & evidence

ORD record
ord-4f660114d0df4e30a2204541c2911ed7
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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