Reaction #6911

Reaction equation

product

N-(1-{6-[(Hydroxyamino)(imino)methyl]quinolin-2-yl}pyrrolidin-3-yl)-2,2-dimethylpropanamide

4-trifluoromethylphenylpropionic acid

EDC

→

2,2-Dimethyl-N-{1-[6-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,2,4-oxadiazol-3-yl)quinolin-2-yl]pyrrolidin-3-yl}propanamide

Solvents

diglyme

Conditions

Workup

1. 1
   Temperaturethe mixture was heated at 110° C. for 2 hr
2. 2
   TemperatureThe mixture was cooled to r.t.
3. 3
   Otherquenched with water
4. 4
   Extractionextracted with excess EtOAc
5. 5
   OtherThe combined extracts were dried over a drying agent
6. 6
   Filtrationfiltered
7. 7
   Otherthe solvent removed under vacuum
8. 8
   OtherThe residue was purified by preparative TLC
9. 9
   Washeluting with EtOAc
10. 10
    Otherto afford the product, MS

Procedure

To a mixture of the product of Step E, (66 mg) in anhydrous diglyme (2 mL) was added 4-trifluoromethylphenylpropionic acid (1.1 eq.) and EDC (2 eq.). The reaction mixture was heated to 50° C. overnight. After approximately 18 h, the mixture was heated at 110° C. for 2 hr. The mixture was cooled to r.t., quenched with water and extracted with excess EtOAc. The combined extracts were dried over a drying agent filtered and the solvent removed under vacuum. The residue was purified by preparative TLC eluting with EtOAc to afford the product, MS: m/z 538.

Source