Hydrochloric Acid → HCID 178463642, compound

HRID 2356709Notes

Reaction equation

HRID 2356709 reaction equation
[C:1]([NH:4][C:5]1[NH:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)[CH3:2].B.[ClH:24].C(=O)([O-])O.[Na+]>O1CCCC1>[ClH:24].[CH2:1]([NH:4][C:5]1[NH:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 178474485HCID 178474485, compound

Product 1

HCID 178463642HCID 178463642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-acetylamino-2-(4-fluorophenyl)-4-phenyl-imidazole (142 mg) in tetrahydrofuran (7 ml) was added 10M borane.tetrahydrofuran complex (12 ml, tetrahydrofuran solution), and the mixture was stirred under argon atmosphere at room temperature for 2 days. To the reaction mixture was slowly added 10% hydrochloric acid, and the mixture was stirred at 60° C. for 10 minutes. After cooling, the mixture was neutralized by adding a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel flush column chromatography (solvent: hexane:ethyl acetate=1:2), and then, treated with hydrogen chloride-methanol solution to obtain 5-ethylamino-2-(4-fluorophenyl)-4-phenyl-imidazole hydrochloride (89 mg) as colorless powder.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by silica gel
  7. customflush column chromatography (solvent: hexane:ethyl acetate=1:2)
  8. additiontreated with hydrogen chloride-methanol solution

Sources & evidence

ORD record
ord-040e6c41df6846359c6865bec1cf7420
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

Loading…