Sulfuric acid magnesium salt (1:1) → N-Methyl-[2-methyl-1-(phenylsulfonyl)-5-(3-pyridyl)-1H-pyrrol-3-yl]methanamine

HRID 554440Notes

Reaction equation

HRID 554440 reaction equation
[CH3:1][C:2]1[N:3]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:6]=1[CH:7]=O.CO.[CH3:26][NH2:27].S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>CO.O1CCCC1>[CH3:26][NH:27][CH2:7][C:6]1[CH:5]=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N:3]([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 866207692-Methyl-1-(phenylsulfonyl)-5-(3-pyridyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 66925089N-Methyl-[2-methyl-1-(phenylsulfonyl)-5-(3-pyridyl)-1H-pyrrol-3-yl]methanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-1-(phenylsulfonyl)-5-(3-pyridyl)-1H-pyrrole-3-carbaldehyde (276 mg) in methanol (2 mL) and tetrahydrofuran (2 mL) were added 40% methylamine methanol solution (1.0 mL) and anhydrous magnesium sulfate (270 mg), and the reaction mixture was stirred at room temperature for 4 hr. To the reaction mixture was added sodium borohydride (43 mg) at room temperature and the mixture was stirred for 30 min. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate) to give a free base of the title compound as a yellow oil. To a solution (4 mL) of the obtained free base in ethanol was added a solution (2 mL) of oxalic acid (18 mg) in ethanol. The mixture was stirred at room temperature for 10 min, and concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as white crystals (yield 103 mg, 59%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-2420a11fc2b6401f8adba48a08a21326
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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