Reacción #612703

Ecuación de reacción

Diisopropylethylamine

product

(5-(4-((4S,5R)-3-(2,2-dichloroacetyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)phenyl)pyridin-2-yl)methyl methanesulfonate

azetidine

HCl

→

title compound

Rendimiento 21.3%

N-((1R,2S)-1-(4-(6-(azetidin-1-ylmethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide

Rendimiento 21.3%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent is removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue dissolved in CH2Cl2 (2 mL)
3. 3
   workup.ADDITIONtrifluoroacetic acid (2 mL) added
4. 4
   Otrothe solvent is removed under reduced pressure
5. 5
   Otrothe crude product purified

Procedimiento

Diisopropylethylamine (2964, 1.68 mmol) is added to the product of Example 20, Step 2 (50 mg, 0.11 mmol) and azetidine.HCl salt (146 mg, 1.12 mmol) in dimethylformamide (1 mL) and the mixture heated to 60° C. for 4 hours. The solvent is removed under reduced pressure and the residue dissolved in CH2Cl2 (2 mL). The mixture is cooled to 0° C. and trifluoroacetic acid (2 mL) added. After 1 hour, the solvent is removed under reduced pressure and the crude product purified using reverse phase HPLC to give the title compound (10 mg): m/z (Cl) M−H 425.1.

Fuente