Reacción #89156

Ecuación de reacción

rac-cis-(2-bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone

pyrazole

(1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine

Cs2CO3

→

title compound

rac-cis-(3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(5-methyl-2-(1H-pyrazol-1-yl)phenyl)methanone

TFA

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed
2. 2
   TemperaturaThe reaction was cooled to RT
3. 3
   OtroThe solvent was removed in vacuo
4. 4
   Otroto obtain the crude which
5. 5
   Otroas purified by preparative-HPLC

Procedimiento

A mixture of rac-cis-(2-bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone (0.0326 g, 0.0693 mmol), pyrazole (0.0094 g, 0.139 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.004 g, 0.0277 mmol), Cs2CO3 (0.045 g, 0.139 mmol) and CuI (0.003 g, 0.0139 mmol) and dioxane (1.0 mL) was degassed and heated overnight at 140° C. The reaction was cooled to RT, and acidified with TFA to pH4-5. The solvent was removed in vacuo to obtain the crude which as purified by preparative-HPLC to obtain the title compound as a TFA salt. ESI-MS (m/z): 458, [M+1]+.

Fuente