Acetone → 3-ethylsulfonyl-N-methyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide

HRID 713667Notes

Reaction equation

CI.[CH2:3]([S:5]([C:8]1[C:9]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:30][CH3:31])([O:28][CH3:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH3:4].[C:32](=O)([O-])[O-].[K+].[K+].CC(C)=O>O.CN(C=O)C>[CH2:3]([S:5]([C:8]1[C:9]([C:14]([N:16]([CH3:32])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:28][CH3:29])([O:30][CH3:31])[C:24]([F:25])([F:27])[F:26])=[CH:19][CH:18]=2)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:6])=[O:7])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

1.0 g of methyl iodide was added to a mixture of 0.12 g of 3-ethylsulfonyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide (Compound of Present Invention 42), 0.15 g of potassium carbonate, 2 mL of acetone and 2 mL of DMF, and the mixture was stirred at 80° C. for 3 hours. Water was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.13 g of 3-ethylsulfonyl-N-methyl-N-[4-(2,2,2-trifluoro-1,1-dimethoxyethyl)phenyl]picolinamide (hereinafter, referred to as Compound of Present Invention 43).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5342da91b2d44a96aff5b2008d6df9e9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09185910B2

Reaction notes

Loading…