Dimethylamine → HCID 21939837, compound

HRID 1242928Notes

Reaction equation

HRID 1242928 reaction equation
CS(Cl)(=O)=O.O[CH2:7][CH2:8][C:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=[CH:12][C:11]=2[CH:10]=1.[CH2:23]([N:25](CC)[CH2:26]C)C.CNC>O1CCCC1.CN(C)C=O>[CH3:23][N:25]([CH3:26])[CH2:7][CH2:8][C:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=[CH:12][C:11]=2[CH:10]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21939867HCID 21939867, compound

Product 1

HCID 21939837HCID 21939837, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (0.0393 ml, 0.469 mmol) was added to a dimethylformamide solution (2 ml) of N-[6-(2-hydroxyethyl)-7,8-dihydro-2-naphthalenyl]acetamide (102 mg, 0.426 mmol) obtained in Reference Example 102 and triethylamine (0.0652 ml, 0.469 mmol) under ice-cooling, which was stirred for 30 minutes. A tetrahydrofuran solution (0.64 ml) of 2N dimethylamine was added to the reaction mixture, which was stirred at 60° C. for 5 hours. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, and extraction was conducted using 1N hydrochloric acid. Potassium carbonate was added to the extract to make it alkaline, and extraction was conducted using ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resulting residue was purified by alumina column chromatography (development solvent; ethyl acetate), to give the titled compound (57.5 mg).

Workup

  1. temperaturecooling
  2. stirringwas stirred at 60° C. for 5 hours
  3. distillationThe solvent was distilled out under reduced pressure
  4. additionEthyl acetate was added to the residue, and extraction
  5. additionPotassium carbonate was added to the
  6. extractionextract
  7. extractionextraction
  8. washThe extract was washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled out under reduced pressure
  11. customThe resulting residue was purified by alumina column chromatography (development solvent; ethyl acetate)

Sources & evidence

ORD record
ord-aefb2dc349c147c997b4c27411343578
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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