Methyl iodide → 6-Fluoro-5-(methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 1436722Notes

Reaction equation

HRID 1436722 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[C:17]([F:18])=[C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[C:17]([F:18])=[C:16]([N:19]([S:20]([CH3:23])(=[O:21])=[O:22])[CH3:25])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 688144606-Fluoro-5-methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688171926-Fluoro-5-(methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid ethyl esterYield 92.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

Dissolve 6-fluoro-5-methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid ethyl ester (0.160 g, 0.444 mmol) in DMF (1.0 mL). Add potassium carbonate (44.4 mg, 0.32 mmol), iodomethane (41.5 μL, 0.67 mmol) and tetrabutylammonium bromide (14.3 mg, 0.04 mmol) to the solution. Stir the resulting slurry at room temperature for 16 h. Quench with saturated aqueous sodium sulfate solution (10 mL) and extract with ethyl acetate (3=30 mL). Combine the organic layers and dry (magnesium sulfate). Azeotrope the residue with xylenes to remove residual DMF. Purify (silica gel chromatography, eluting with 40:60 ethyl acetate:dichloromethane) to give the title compound as a solid (111 mg, 67%).

Workup

  1. customQuench with saturated aqueous sodium sulfate solution (10 mL)
  2. extractionextract with ethyl acetate (3=30 mL)
  3. dry with materialCombine the organic layers and dry (magnesium sulfate)
  4. customAzeotrope the residue with xylenes to remove residual DMF
  5. customPurify
  6. wash(silica gel chromatography, eluting with 40:60 ethyl acetate:dichloromethane)

Sources & evidence

ORD record
ord-3aca65c6cc704de9982f6fa5209fbcbe
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…