4-Methylpyrazole → HCID 71233130, compound

Participants

Reaction Conditions

Reaction Steps

To a sealed tube was added tert-butyl (1R,2R)-2-((S)-1-(4-iodophenyl)piperidin-3-ylamino)cyclohexylcarbamate (150 mg, 0.300 mmol), 4-methyl-1H-pyrazole (29.6 mg, 0.360 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (8.54 mg, 0.060 mmol), K2CO3 (87 mg, 0.631 mmol) and copper(I) iodide (5.72 mg, 0.030 mmol). The reaction was bubbled with argon for 2 min. The reaction vessel was sealed and the reaction was stirred at 100° C. for 16 hrs. After this time, the reaction was cooled to rt and diluted with water. The layers were separated and aqueous solution was extracted with EtOAc (2×30 ml). The combined organic layers were washed with saturated aqueous NaCl (30 ml), dried over Na2SO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 20-100% EtOAc/Hex to give tert-butyl (1R,2R)-2-((S)-1-(4-(4-methyl-1H-pyrazol-1-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate (86 mg, 0.190 mmol, 63.1% yield). Anal. Calcd. for C26H39N5O2 m/z 453.5, found: 454.4 (M+H)+.

Provenance & Evidence