Methyl iodide → HCID 57678971, compound

HRID 492090Notes

Reaction equation

HRID 492090 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)(=[O:22])=[O:21])=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1)(C)(C)C.[C:31](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([N:19]([CH3:31])[S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][C:18]1=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57678967HCID 57678967, compound

Product 1

HCID 57678971HCID 57678971, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 0.22 grams (0.524 mmole) (+/−)-[6-(3-fluoro-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester in 10 mL DMF was added 0.08 grams (0.576 mmole) potassium carbonate and 0.033 mL (0.524 mmole) iodomethane. The reaction mixture was stirred at 23° C. for 0.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water saturated aqueous sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was dissolved in 3 mL warm TFA and immediately concentrated under reduced pressure. The residue was partitioned between saturated aqueous sodium carbonate ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-fluoro-N-methyl-benzenesulfonamide was isolated as the crystalline oxalate salt, 0.06 grams (18%), m.p. 176-177° C., M+H=349.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water saturated aqueous sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 3 mL
  6. temperaturewarm TFA
  7. concentrationimmediately concentrated under reduced pressure
  8. customThe residue was partitioned between saturated aqueous sodium carbonate ethyl acetate
  9. dry with materialThe organic phase was dried (magnesium sulfate)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-810c6ddd14584e439a42ce18c42a3cb7
Source dataset
uspto-grants-2009_05
Patent number
US07531577B2

Reaction notes

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