Cyclohexylamine → 2-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-2,N-dicyclohexyl-acetamide

Participants

Reaction Steps

To an ice cold solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid (9 mg, 24 μmol and cyclohexylamine (2.3 μl, 24 μmol; CAS Reg. No. 108-91-8) in CH2Cl2 (1 ml) under an argon atmosphere was added bromotripyrrolidinophosphonium hexafluorophosphate (17 mg, 36 umol) and N,N-diisopropylethylamine (10 ul, 72 umol). The reaction mixture was stirred for 5 d at ambient temperature, poured onto ice water/1 N aqueous NaOH solution 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/1 N aqueous HCl solution 1/1 and brine and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and the residue was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (5 mg, 11 μmol; 46%) as colorless foam. MS: m/e=450.3 [M+H+].

Provenance & Evidence