Hydrochloric Acid → HCID 66925180, compound

HRID 554438Notes

Reaction equation

HRID 554438 reaction equation
[C:1]1([S:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][C:12]([CH:21]=[O:22])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[OH:24].[CH3:25][NH2:26].[BH4-].[Na+].Cl.[C:30](=[O:33])([O-:32])O.[Na+]>CO>[C:21]([OH:22])(=[O:24])[C:30]([OH:32])=[O:33].[CH3:25][NH:26][CH2:21][C:12]1[CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 862327121-(Phenylsulfonyl)-5-(2-pyridinyl)-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 66925180HCID 66925180, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Phenylsulfonyl)-5-(pyridin-2-yl)-1H-pyrrole-3-carbaldehyde (78 mg) was dissolved in methanol (10 mL), 40% methylamine methanol solution (100 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (29 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (20 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 purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→7:3) and dissolved in ethyl acetate (10 mL). To the solution was added oxalic acid (50 mg) and the mixture was stirred for 15 min. The crystallized crystals were collected by filtration to give the title compound as colorless crystals (yield 47 mg, 45%).

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. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→7:3)
  8. dissolutiondissolved in ethyl acetate (10 mL)
  9. additionTo the solution was added oxalic acid (50 mg)
  10. stirringthe mixture was stirred for 15 min
  11. filtrationThe crystallized crystals were collected by filtration

Sources & evidence

ORD record
ord-4d36db60290444c49dce9047e21f1369
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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