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

HRID 732583Notes

Reaction equation

HRID 732583 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-8b27f292fcdc459dba97deb96b4cc1ed
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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