Hydrochloric Acid → 5-Phenylamino-pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

DIPEA (90 mg, 0.12 mL, 0.7 mmol) was added drop wise to 5-(phenyl-amino)-pyridine-2-carboxylic acid (50 mg, 0.23 mmol) in DMF (5 mL). EDCI (111 mg, 0.58 mmol) and HOBT (37 mg, 0.28 mmol) were added consecutively and, after 10 minutes, 2-amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (125 mg, 0.28 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent) to afford 55 mg (44% yield) of 5-phenylamino-pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 99.28%. 1H-NMR (DMSO-d6): δ 8.9 (s, 1H), 8.5 (t, 1H), 7.9 (m, 2H), 7.6 (d, 3H), 7.4 (t, 2H), 7.2 (d, 2H), 7.0 (t, 1H), 4.2 (d, 2H), 3.6 (m, 5H), 3.2 (m, 3H).

1. extractionthe product was extracted with EtOAc
2. washthe organic layer was washed with brine
3. dry with materialThe organic phase was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto get the residue
6. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent)

ORD-Eintrag

ord-8beea38eef024836867f355cbb953f1f

Quelldatensatz

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07842696B2