Reacción #165833

Ecuación de reacción

[[3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbonyl]amino]thiourea

→

sub-title compound

Rendimiento 86.1%

5-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazol-2-amine

Rendimiento 86.1%

Disolventes

DCE

EDC

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture heated
2. 2
   Temperaturaat reflux for 22 h
3. 3
   OtroThe solvent was removed in vacuo
4. 4
   Otrothe residue partitioned between EtOAc and water
5. 5
   ExtracciónThe aqueous layer was extracted with EtOAc (3×10 mL)
6. 6
   Filtraciónthe combined organic extracts dried MgSO4, filtered
7. 7
   Concentraciónconcentrated in vacuo

Procedimiento

EDC (109.3 mg, 0.5704 mmol) was added to a stirred suspension of [[3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbonyl]amino]thiourea (150 mg, 0.3803 mmol) in DCE (3.000 mL) and the reaction mixture heated at reflux for 22 h. The solvent was removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (3×10 mL) and the combined organic extracts dried MgSO4, filtered and concentrated in vacuo to give the sub-title compound as a yellow solid (118 mg, 86%) 1H NMR (400 MHz, DMSO) d 1.19 (d, 6H), 3.45 (dt, 1H), 7.65-7.80 (m, 4H), 7.95 (d, 2H), 8.26 (d, 2H) and 8.89 (s, 1H) ppm; MS (ES+) 361.0

Fuente