2-Furylglyoxylic acid → 1-(4-(2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-2-(furan-2-yl)ethane-1,2-dione

4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one TFA salt (155 mg, 0.32 mmol), 2-(furan-2-yl)-2-oxoacetic acid (278 mg, 1.98 mmol), DIPEA (0.5 ml, 3 mmol), and HATU (251 mg, 0.66 mmol) were mixed in DMF (30 ml), the resulting reaction mixture was stirred at room temperature for 45 h until the reaction finished (monitored by TLC). The reaction mixture was then partitioned between DCM and water (100 ml each, and the water phase was extracted with DCM (50 ml). The combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=1:3) to afford the desired product (20 mg, 20.4%) as a light yellow solid.

1. customthe resulting reaction mixture
2. customThe reaction mixture was then partitioned between DCM and water (100 ml each
3. extractionthe water phase was extracted with DCM (50 ml)
4. washThe combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated
8. customto yield the crude product
9. customThen the crude product was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=1:3)

ORD record

ord-91929331115247e1b9518bec22a414d3

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999985B2