Dichloromethane → HCID 89832397, compound

(E)-4,4,4-Trifluorobut-2-enoic acid (17 mg, 0.12 mmol) was dissolved in dichloromethane (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (11 μl, 0.12 mmol) and the solution was stirred at room temperature for 10 minutes. This solution was added to a solution of N-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)ethane-1,2-diamine (17 mg, 0.1 mmol) and TEA (42 μl, 0.3 mmol) in a mixture of anhydrous dichloromethane (1 ml) and anhydrous DMF (1 ml) and the resulting mixture was stirred at room temperature. After one hour, additional acid chloride (0.12 mmol as prepared above) was added and stirring was continued for one hour. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and brine, dried (magnesium sulfate), concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 5% to 100% acetonitrile) to yield 8 mg of a solid (0.019 mmol, 19%).

1. stirringthe resulting mixture was stirred at room temperature
2. waitAfter one hour
3. stirringstirring
4. waitwas continued for one hour
5. washwashed with saturated sodium bicarbonate solution and brine
6. dry with materialdried (magnesium sulfate)
7. concentrationconcentrated under reduced pressure
8. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 5% to 100% acetonitrile)

ORD record

ord-39224f7330914c96b6dfef217de3313c

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321724B2