Reacción #1730494

Ecuación de reacción

4-(dibenzylamino)benzoic acid

EDC

HOBt

phenylenediamine

→

N-(2-aminophenyl)-4-(dibenzylamino)benzamide

Disolventes

EtOAc

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe crude reaction mixture
2. 2
   Lavadowashed with sat.'d aq. NaHCO3 (1×10 mL)
3. 3
   SecadoThe organic layer was dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe crude residue was purified by reverse-phase chromatography (20-100% MeCN/H2O with 0.05% TFA)
7. 7
   workup.ADDITIONdiluted with EtOAc (20 mL)
8. 8
   Lavadowashed with sat.'d aq. NaHCO3 (1×10 mL)
9. 9
   SecadoThe organic layer was dried over MgSO4
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 4-(dibenzylamino)benzoic acid (50 mg, 0.16 mmol) in DMF was added EDC (181 mg, 0.95 mmol), HOBt (128 mg, 0.95 mmol) and phenylenediamine (171 mg, 1.58 mmol) were which was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (20 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (20-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to gave the desired N-(2-aminophenyl)-4-(dibenzylamino)benzamide: 1H NMR (600 MHz, MeOH-d4) δ 7.83 (d, J=9.0 Hz, 2H), 7.31 (m, 6H), 7.25 (m, 8H), 6.81 (d, J=9.1 Hz, 2H), 4.79 (s, 4H); cal'd 408.2 (MH+), exp 408.2 (MH+).

Fuente