Reaction #41420

Reaction equation

5-methyl-[1,3,4]oxadiazol carboxylic acid potassium salt

(1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine

HATU

ethyldiisopropylamine

→

N-{(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenylpropan-2-yl}-5-methyl-[1,3,4]oxadiazol-2-carboxamide

Solvents

dichloromethane

DMF

DMF

Conditions

Workup

1. 1
   workup.WAITthe stirring was continued for 24 h at r.t
2. 2
   Filtrationfiltrated through a path of silica gel
3. 3
   OtherSolvent was removed under reduced pressure
4. 4
   Otherthe residue was purified by preparative TLC on silica gel (hexane/acetone 50%)

Procedure

To a stirred solution of HATU (630 mg, 1.66 mmol) in DMF (1 ml) was added ethyldiisopropylamine (570 μl, 3.3 mmol), followed by 5-methyl-[1,3,4]oxadiazol carboxylic acid potassium salt (138 mg, 830 μmol) and stirred for 20 min. Then (1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine (300 mg, 830 mmol) in DMF (1 ml) was added to the brown/red solution and the stirring was continued for 24 h at r.t. The mixture was diluted by dichloromethane and filtrated through a path of silica gel. Solvent was removed under reduced pressure, and the residue was purified by preparative TLC on silica gel (hexane/acetone 50%). Yield 82 mg (21%).

Source