Thionyl Chloride → Methyl alpha-phenyl-1-[4-[[[4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl]carbonyl]amino]phenyl]-4-piperidineacetate

DMF (0.5 ml) was added to a solution of 4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxylic acid (0.014 mole) in DCM (50 ml) and thionyl chloride (0.028 mole). The mixture was stirred and refluxed for one hour. The solvent was evaporated. DCM (50 ml) was added twice and the solvent was evaporated. The residue was dissolved in DCM (20 ml) and this solution was added to a mixture of intermediate (15) (0.014 mole) and DIPEA (0.028 mole) in DCM (80 ml). The mixture was stirred at room temperature for three hours and washed with water. The organic layer was dried and the solvent was evaporated. The residue was crystallized from 2-propanol. The precipitate was filtered off and dried, yielding 6.2 g of methyl α-phenyl-1-[4-[[[4′-(trifluoromethyl)-[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-4-piperidineacetate (melting point 151° C.) identified as compound No. 39 in the following table F-1.

1. temperaturerefluxed for one hour
2. customThe solvent was evaporated
3. additionDCM (50 ml) was added twice
4. customthe solvent was evaporated
5. dissolutionThe residue was dissolved in DCM (20 ml)
6. stirringThe mixture was stirred at room temperature for three hours
7. washwashed with water
8. customThe organic layer was dried
9. customthe solvent was evaporated
10. customThe residue was crystallized from 2-propanol
11. filtrationThe precipitate was filtered off
12. customdried

ORD 기록

ord-ecb9d48ff54045c29a2df5c7fd9b35d7

출처 데이터셋

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07528154B2