Oxalyl chloride → Methyl 2-[1-(2-methyl-4-quinolyl)-4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-2-yl]acetate

(E)-4,4,4-Trifluorobut-2-enoic acid (15.4 mg, 0.08 mmol) was dissolved in DCM (1 ml), oxalyl chloride was added (9.4 μl, 0.11 mmol) followed by a drop of DMF. The mixture was stirred for 10 minutes at room temperature. Methyl 2-[1-(2-methyl-4-quinolyl)piperazin-2-yl]acetate (33.6 mg, 0.1 mmol) was dissolved in DMF (1 ml) together with diisopropylethylamine (44 μl, 0.25 mmol), the solutions were combined and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.9 mg (0.0093 mmol, 9%).

1. stirringthe resulting mixture was stirred at room temperature overnight
2. customThe volatiles were removed under reduced pressure
3. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
4. customto yield 3.9 mg (0.0093 mmol, 9%)

ORD record

ord-dd90ecebe18949c88a1ffafc59729ca2

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883791B2