Hydrochloric Acid → HCID 178482480, compound

HRID 2356706Notes

Reaction equation

HRID 2356706 reaction equation
[CH:1]([NH:3][C:4]1[NH:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O.B.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][NH:3][C:4]1[NH:8][C:7]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[N:6][C:5]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 178522621HCID 178522621, compound

Product 1

HCID 178482480HCID 178482480, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-formylamino-2-(4-fluorophenyl)-4-phenylimidazole (1.06 g) in tetrahydrofuran (15 ml) was added dropwise 10M borane.dimethylsulfide complex (1.90 ml), and the mixture was stirred under argon atmosphere at room temperature for 2.5 hours. 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) to obtain 5-methylamino-2-(4-fluorophenyl)-4-phenylimidazole (702 mg) as colorless powder. 88 mg of the product was treated with hydrogen chloride-methanol solution to obtain the hydrochloride salt (84 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)

Sources & evidence

ORD record
ord-23dabb57598545c7ab85cefbac18718b
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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