Reacción #10168

Ecuación de reacción

iodomethane

iodomethane

triethylamine

Methyl 4′-({[(1-aminocyclopropyl)carbonyl]amino}methyl)-1,1′-biphenyl-2-carboxylate

→

methyl 4′-[({[1-(methylamino)cyclo-propyl]carbonyl}amino)methyl]-1,1′-biphenyl-2-carboxylate

Rendimiento 34.8%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas observed at ambient temperature
2. 2
   Temperaturathe reaction mixture was heated
3. 3
   Temperaturato reflux for about two days
4. 4
   OtroAfter two days >50% of the starting material was consumed
5. 5
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
6. 6
   Lavadoeluting with 1–10% MeOH in DCM

Procedimiento

Methyl 4′-({[(1-aminocyclopropyl)carbonyl]amino}methyl)-1,1′-biphenyl-2-carboxylate (200 mg, 0.62 mmol), prepared according to Example 1, was dissolved in 5 mL of DCM along with iodomethane (130 mg, 0.93 mmol) and triethylamine (75 mg, 0.74 mmol). After no reaction was observed at ambient temperature, the reaction mixture was heated to reflux for about two days. After the first day, additional iodomethane was added (ca. 3–5 equiv.). After two days >50% of the starting material was consumed. The reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel chromatography eluting with 1–10% MeOH in DCM to afford 73 mg of methyl 4′-[({[1-(methylamino)cyclo-propyl]carbonyl}amino)methyl]-1,1′-biphenyl-2-carboxylate.

Fuente