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

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.

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

ORD record

ord-f0f1584f1b2d49ca9b8b4bd71be46f62

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492405B2