Réaction #309065

Équation de réaction

4-(Pyridin-4-yloxy)phenylamine

5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-ylamine

CDI

→

desired product

Rendement 68.0%

1-[5-tert-butyl-2-(4-nitro-phenyl)-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)-phenyl]-urea

Rendement 68.0%

Solvants

DCE

DCE

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe solution was stirred under N2 at room temperature for 7 h
2. 2
   AutreThe reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL)
3. 3
   LavageThe organic layer was washed with brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated at reduced pressure
6. 6
   AutreThe crude residue was purified by MPLC (1:1 hexanes/EtOAc)

Mode opératoire

To a solution of 5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-ylamine (5.0 g, 19.2 mmol) in anhydrous DCE (2 mL) was added CDI (3.5 g, 21.1 mmol), and the reaction was stirred under N2 at room temperature for 18 h. 4-(Pyridin-4-yloxy)phenylamine (3.3 g, 17.7 mmol, Dumas et al., U.S. pat. appl. US2002065296 (2002)) in DCE (12 mL) was added to the reaction, and the solution was stirred under N2 at room temperature for 7 h. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The crude residue was purified by MPLC (1:1 hexanes/EtOAc) to give 5.6 g (68%) of the desired product. 1H-NMR (DMSO-d6) δ 9.21 (s, 1H), 8.68 (s, 1H), 8.43 (d, J=6.3 Hz, 2H), 8.36 (d, J=7.2 Hz, 2H), 7.90 (d, J=6.9 Hz, 2H), 7.50 (d, J=6.9 Hz, 2H), 7.09 (d, J=6.6 Hz, 2H), 6.86 (d, J=5.7 Hz, 2H), 6.44 (s, 1H), 1.29 (s, 9H); MS LC-MS [M+H]+=473, RT=2.60 min.

Source