Ammonium Chloride → Ethyl 4-ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylate

HRID 453596Notes

Reaction equation

HRID 453596 reaction equation
[O-]CC.[Na+].[CH2:5]([N:7]1[C:11]([CH:12]=O)=[CH:10][C:9]([N:14]([CH3:23])[S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])=[CH:8]1)[CH3:6].[N:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N+]=[N-].[Cl-].[NH4+]>C(O)C>[CH2:5]([N:7]1[C:11]2[CH:12]=[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[NH:24][C:10]=2[C:9]([N:14]([CH3:23])[S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])=[CH:8]1)[CH3:6]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 59411382N-(1-ethyl-5-formyl-1H-pyrrol-3-yl)-N-methylthiophene-2-sulfonamide

Product 1

HCID 59411371Ethyl 4-ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution (150 mL) of sodium ethoxide (8.3 g) in ethanol was added dropwise a mixture of N-(1-ethyl-5-formyl-1H-pyrrol-3-yl)-N-methylthiophene-2-sulfonamide (8.5 g) and ethyl azidoacetate (16.5 g) under ice-cooling. After the completion of the dropwise addition, the mixture was stirred for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was concentrated. The obtained residue was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:1, volume ratio). The obtained yellow oil was dissolved in toluene (50 mL), and the mixture was stirred at 110° C. for 1 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography to give ethyl 4-ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylate (1.12 g, yield 32%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 122° C.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. concentrationthe mixture was concentrated
  4. extractionThe obtained residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. washeluted with ethyl acetate-hexane (1:1, volume ratio)
  9. dissolutionThe obtained yellow oil was dissolved in toluene (50 mL)
  10. stirringthe mixture was stirred at 110° C. for 1 hr
  11. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f0f1584f1b2d49ca9b8b4bd71be46f62
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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