Diisopropylethylamine → N-[[5-tert-butyl-2-(3-chlorophenyl)-2H-pyrazol-3-yl]-methyl]-2-(3-fluoro-4-methylsulfonyl-phenyl)propionamide

To a solution of (3-tert-butyl-1-(3-chloro-4-fluorophenyl)-1H-pyrazol-5-yl)methanamine (49 mg, 0.189 mmol) in DCM (1.3 mL) at room temperature and under nitrogen atmosphere was added 1-chloro-N,N,2-trimethyl-1-propenylamine (48 μL, 0.369 mmol), After 1 h of stirring were added 2-(3-fluoro-4-(methylsulfonyl)phenyl)propanoic acid (93 mg, 0.378 mmol) and N-ethyldiisopropylamine (0.11 mL, 0.662 mmol). The reaction mixture was stirred overnight at room temperature, washed with NaHCO3 solution (2×10 mL), dried over sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by column chromatography (eluent: ethyl acetate/cyclohexane (2:1)) to give pure N-[[5-tert-butyl-2-(3-chlorophenyl)-2H-pyrazol-3-yl]-methyl]-2-(3-fluoro-4-methylsulfonyl-phenyl)-propionamide (example compound D1) (66 mg, 71%).

1. stirringThe reaction mixture was stirred overnight at room temperature
2. washwashed with NaHCO3 solution (2×10 mL)
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe obtained crude product
6. customwas purified by column chromatography (eluent: ethyl acetate/cyclohexane (2:1))

ORDレコード

ord-db17c32d6a054c7aa84dc01d55bd0ce3

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08946204B2