Reacción #91097

Ecuación de reacción

3-(benzenesulfonyl-benzyl-amino)-benzoic acid

6-amino-1H-indazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

mercaptobenzothiazole

triethylamine

→

title compound

Rendimiento 45.7%

3-(Benzenesulfonyl-benzyl-amino)-N-(1H-indazol-6-yl)-benzamide

Rendimiento 45.7%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was quenched with water (10 ml)
2. 2
   Extracciónextracted with dichloromethane (3×7 ml)
3. 3
   Secadodried (PTFE frit)
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe crude residue was purified by preparative TLC (10% diethyl ether in dichloromethane)

Procedimiento

A solution of 3-(benzenesulfonyl-benzyl-amino)-benzoic acid (25 mg, 0.068 mmol), 6-amino-1H-indazole (18 mg, 0.136 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (15 mg, 0.075 mmol), mercaptobenzothiazole (2 mg, 0.007 mmol) and triethylamine (24 μl, 0.17 mmol) in dry acetonitrile (2 ml) were stirred at room temperature for 15 hrs. The reaction mixture was quenched with water (10 ml) and extracted with dichloromethane (3×7 ml). The organics were combined, dried (PTFE frit) and concentrated in vacuo. The crude residue was purified by preparative TLC (10% diethyl ether in dichloromethane) to afford the title compound as a brown solid (15 mg, 45%). HPLC retention time 5.80 min. Mass spectrum (ES+) m/z 483 (M+H).

Fuente