Hydrochloric Acid → HCID 66924954, compound

HRID 554430Notes

Reaction equation

HRID 554430 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH:26]=O)[CH:9]=1.CO.[CH3:30][NH2:31].[BH4-].[Na+].[ClH:34].C(=O)([O-])O.[Na+]>CO>[ClH:34].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:26][NH:31][CH3:30])[CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86620782HCID 86620782, compound

Product 1

HCID 66924954HCID 66924954, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2-Fluorophenyl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde (550 mg) was dissolved in methanol (55 mL), 40% methylamine methanol solution (1.05 g) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (154 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (100 mL) was added, and the mixture was stirred for 5 min. The reaction mixture was alkalized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in methanol (10 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 400 mg, 65%).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was stirred for 5 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in methanol (10 mL)
  8. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c3244954ea594778995d74e65169f0a1
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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