Triethylamine → HCID 131731126, compound

At a temperature of 0° C., a solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.243 g; 1.24 mmol) in dichloromethane (5 ml) was added dropwise to a stirred solution of (S)-2-(2,4,6-trichloro-phenoxymethyl)-pyrrolidine hydrochloride (0.35 g; 1.24 mmol), which was prepared as described in example P12, and triethylamine (0.35 ml; 2.48 mmol) in dichloromethane (10 ml). The ice bath was removed and reaction mixture was allowed stirring for 3 hours. The reaction mixture was washed with 1M NaOH (10 ml), 2M HCl (10 ml) and saturated NaCl (50 ml) and then dried over Na2SO4. After removal of the solvent, the residue (0.45 g in the form of an oil) was purified by flash chromatography over silica gel (eluent:cyclohexane/ethyl acetate 2:8). 0.27 g (50% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-[(S)-2-(2,4,6-trichloro-phenoxymethyl)-pyrrolidin-1-yl]-methanone was obtained in form of an oil which solified after standing.

1. customwas prepared
2. customThe ice bath was removed
3. customreaction mixture
4. washThe reaction mixture was washed with 1M NaOH (10 ml), 2M HCl (10 ml) and saturated NaCl (50 ml)
5. dry with materialdried over Na2SO4
6. customAfter removal of the solvent
7. customthe residue (0.45 g in the form of an oil) was purified by flash chromatography over silica gel (eluent:cyclohexane/ethyl acetate 2:8)

ORD record

ord-d3026b70012d4cb1b0fd8497d4ff2b66

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623902B2