Reacción #330145

Ecuación de reacción

4-fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

(S)-2-tertbutoxycarbonylamino-3-methylbutyric acid

HOAt

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

{(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]-2-methylpropyl}carbamic acid tert-butyl ester

Rendimiento 65.4%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was partitioned between DCM
2. 2
   SecadoThe organic layer was dried (MgSO4)
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otrothe resulting residue purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane)

Procedimiento

To a solution of 4-fluoro-N2-pyridin-3-ylbenzene-1,2-diamine (685 mg, 3.0 mmol) in DCM (18 mL) at 0° C. were added (S)-2-tertbutoxycarbonylamino-3-methylbutyric acid (720 mg, 3.3 mmol), HOAt (0.450 g, 3.3 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.63 g, 3.3 mmol) and the resulting mixture stirred at 0° C. for 2 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane) to afford {(S)-1-[4-fluoro-2-(pyridin-3-ylamino)phenylcarbamoyl]-2-methylpropyl}carbamic acid tert-butyl ester (790 mg). LCMS (Method J): RT 2.10 min [M+H]+ 403.3

Fuente