Oxalyl chloride → 5-Chloro-4,6-dimethyl-2-[4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-1-yl]pyridine-3-carbonitrile

(E)-4,4,4-Trifluorobut-2-enoic acid (25 mg, 0.18 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (16 μl, 0.18 mol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 10 minutes. This solution was added to a solution of 5-chloro-4,6-dimethyl-2-piperazin-1-yl-pyridine-3-carbonitrile (38 mg, 0.15 mmol) and DIPEA (79 μl, 0.45 mmol) in anhydrous DCM (2 ml) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 2.7 mg of a solid (0.007 mmol, 5%).

1. stirringthe resulting mixture was stirred at room temperature overnight
2. concentrationThe mixture was concentrated under reduced pressure
3. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

ORDレコード

ord-f428f8eff9414f84a16ccd7023cedb5c

出典データセット

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09260441B2