p-Toluenesulfonic acid → HCID 18367506, compound

HRID 379613Notes

Reaction equation

HRID 379613 reaction equation
O[C:2]1([C:8]2[NH:9][C:10]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>>[C:2]1([C:8]2[NH:9][C:10]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 18367514HCID 18367514, compound

Product 1

HCID 18367506HCID 18367506, compound

Procedure

The product of Example 7, 2-((1-hydroxy)cyclohexyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole (50 mg 0.15 mmol) is dissolved in toulene (100 ml) and refluxed with pTsOH (100 mg) for 15 min. The reaction mixture is poured on saturated NaHCO3 and extracted 3× with ethyl acetate. The combined organic phases are dried over Na2SO4, evaporated to dryness and chromatographed (SiO2 acetone/hexane 4/6) to render the title compound as white crystals (38 mg 81%),

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. customevaporated to dryness
  4. customchromatographed (SiO2 acetone/hexane 4/6)

Sources & evidence

ORD record
ord-486f53b2fa1549a09afc1f22bf8e5132
Source dataset
uspto-grants-2001_10
Patent number
US06300347B1

Reaction notes

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