Triethylamine → 1,4-Dimethyl-3-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-6-(3-trifluoromethyl-phenyl)-1H-pyridin-2-one

A solution of 0.16 g (0.5 mmol) of 1,4-dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid (intermediate 5) in 5 ml of CH2Cl2 was treated at RT with two drops of DMF; then, 0.05 ml=0.074 g (0.6 mmol) of oxalyl chloride was added and the reaction mixture was stirred for 30 min at RT. After removal of the solvents by evaporation in a high vacuum, the residue was dissolved again in 10 ml of CH2Cl2 and the solution was cooled down to 0° C.; then, 0.29 ml=0.21 g (2.1 mmol) of Et3N was added while stirring, followed by 0.081 g (0.5 mmol) of 4-pyrrolidin-1-yl-piperidine. The reaction mixture was subsequently warmed up to RT. After 3 hours, it was poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 95:5) to give 0.20 g (85%) of the title compound as light yellow solid. MS: 448.2 (MH+).

1. customAfter removal of the solvents
2. customby evaporation in a high vacuum
3. dissolutionthe residue was dissolved again in 10 ml of CH2Cl2
4. temperaturethe solution was cooled down to 0° C.
5. stirringwhile stirring
6. temperatureThe reaction mixture was subsequently warmed up to RT
7. waitAfter 3 hours
8. additionit was poured
9. extractionextracted twice with CH2Cl2
10. washthe organic phases were washed with water
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. customevaporated
14. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 95:5)

ORDレコード

ord-0fe8cc21214342158d41335d7a9b0766

出典データセット

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08227613B2