Reacción #88023

Ecuación de reacción

methyl 3-(methylsulfonamido)thiophene-2-carboxylate

4-(2-chloroethyl)morpholine hydrochloride

DCM MeOH

potassium carbonate

→

methyl 3-(N-(2-morpholinoethyl)-methylsulfonamido)thiophene-2-carboxylate

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared in an analogous manner
2. 2
   OtroThe solvent was evaporated
3. 3
   workup.ADDITIONthe residue was diluted with EtOAc
4. 4
   Lavadowashed with H2O and brine
5. 5
   Secadothe organic layer was dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe crude was purified by flash chromatography on silica gel (DCM/EtOAc=8/2 to 7/3

Procedimiento

A mixture of methyl 3-(methylsulfonamido)thiophene-2-carboxylate (prepared in an analogous manner as described in Example 8, Scheme 8, Step 1, 500 mg, 2.125 mmol), 4-(2-chloroethyl)morpholine hydrochloride (435 mg, 2.338 mmol) and potassium carbonate (646 mg, 4.68 mmol) in dry DMF (13 ml) was heated at 80° C. for 5 h and stirred at RT for 3 days. The solvent was evaporated, the residue was diluted with EtOAc and washed with H2O and brine; the organic layer was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography on silica gel (DCM/EtOAc=8/2 to 7/3 and then DCM/MeOH=95/5) to afford methyl 3-(N-(2-morpholinoethyl)-methylsulfonamido)thiophene-2-carboxylate (Int. 50) (655 mg, 1.880 mmol, MS/ESI+ 348.9 [MH]+).

Fuente