Pyruvic Acid → 1-(4-(2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)propane-1,2-dione

4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one TFA salt (157.5 mg, 0.34 mmol), 2-oxopropanoic acid (0.15 ml (d=1.26), 2.15 mmol), DIPEA (0.5 ml, 3 mmol), and HATU (258.6 mg, 0.68 mmol) were mixed in DMF (20 ml), the resulting reaction mixture was stirred at room temperature for 60 h until the reaction finished (monitored by TLC). The reaction mixture was then partitioned between DCM and water (50 ml each, 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=1:2) to afford the desired product (20 mg, 13.5%) as a light yellow solid.

1. customthe resulting reaction mixture
2. customThe reaction mixture was then partitioned between DCM and water (50 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=1:2)

ORD record

ord-d8b653b943ac48cc823d6464a40211c2

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999985B2