Hydrochloric Acid → HCID 178483105, compound

HRID 2356707Notes

Reaction equation

HRID 2356707 reaction equation
C([CH2:3][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.B.[ClH:24].[C:25](=O)([O-])O.[Na+]>O1CCCC1>[ClH:24].[CH3:25][N:4]([CH3:3])[C:5]1[NH:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[N:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 178521299HCID 178521299, compound

Product 1

HCID 178483105HCID 178483105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-formylmethylamino-2-(4-fluorophenyl)-4-phenylimidazole (200 mg) in tetrahydrofuran (5 ml) was added dropwise 10M borane.dimethylsulfide complex (0.34 ml), and the mixture was stirred under argon atmosphere at room temperature for overnight. To the reaction mixture was slowly added 10% hydrochloric acid, and the mixture was refluxed for one hour. 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=5:1), and then, treated with hydrogen chloride-methanol solution to obtain 5-dimethylamino-2-(4-fluorophenyl)-4-phenylimidazole hydrochloride (174 mg) as colorless powder.

Workup

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

Sources & evidence

ORD record
ord-85c38adc09fe432a889fa0d9f7100495
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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