Phenylacetic Acid → 3-Amino-6-bromo-N'-(2-phenylacetyl)-5-(trifluoromethyl)pyrazine-2-carbohydrazide

To a stirred solution of phenyl acetic acid (95.0 mg, 0.698 mmol) in NMP (6 ml) was added a solution 3-amino-6-bromo-5-(trifluoromethyl)pyrazine-2-carbohydrazide (step 1) (250 mg, 0.837 mmol) in NMP (6 ml) followed by DIPEA (609 ul, 3.49 mmol). The resulting mixture was treated with HATU (398 mg, 1.047 mmol) portionwise and stirred at RT for 90 min. The mixture was added to EtOAc (50 ml) and washed with 0.1M NaOH (50 ml). The aqueous layer was back extracted with EtOAc (50 ml). The combined organic portions were washed with water (50 ml), brine (50 ml), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 1:1 EtOAc/iso-hexane to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.65 (1H, s), 10.29 (1H, s), 8.02 (2H, s), 7.30 (5H, m), 3.52 (2H, s). 19F NMR (400 MHz, DMSO-d6) δ-66 (s, CF3).

1. washwashed with 0.1M NaOH (50 ml)
2. extractionThe aqueous layer was back extracted with EtOAc (50 ml)
3. washThe combined organic portions were washed with water (50 ml), brine (50 ml)
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customThe crude product was purified by chromatography on silica eluting with 1:1 EtOAc/iso-hexane

ORD record

ord-0453d4c51ba2455c88791f6339d4fb24

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034879B2