Hydrochloric Acid → HCID 66925142, compound

HRID 554435Notes

Reaction equation

HRID 554435 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([S:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[CH:17][C:16]([CH:29]=O)=[CH:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].CO.[CH3:33][NH2:34].[BH4-].[Na+].[ClH:37].C(=O)([O-])O.[Na+]>CO>[ClH:37].[CH3:33][NH:34][CH2:29][C:16]1[CH:17]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])[N:14]([S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)(=[O:13])=[O:12])[CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86620786HCID 86620786, compound

Product 1

HCID 66925142HCID 66925142, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{[3-(Methylsulfonyl)phenyl]sulfonyl}-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (300 mg) was dissolved in methanol (30 mL), 40% methylamine methanol solution (510 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (75 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (30 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 methanol (5 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 214 mg, 64%).

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 methanol (5 mL)
  9. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5f86e1cddb844e748326b2a461674dd6
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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