Triethylamine → HCID 21939737, compound

HRID 1242927Notes

Reaction equation

HRID 1242927 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][CH3:27])[CH3:24].N1CCCC1>CN(C)C=O>[N:25]1([CH2:7][CH2:8][C:9]2[CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=[CH:12][C:11]=3[CH:10]=2)[CH2:26][CH2:27][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 21939867HCID 21939867, compound

Product 1

HCID 21939737HCID 21939737, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonyl chloride (0.131 ml, 1.69 mmol) was added to a dimethylformamide solution (7 ml) of N-[6-(2-hydroxyethyl)-7,8-dihydro-2-naphthalenyl]acetamide (355 mg, 1.53 mmol) obtained in Reference Example 102 and triethylamine (0.235 ml, 1.69 mmol) under ice-cooling, which was stirred for 30 minutes. Pyrrolidine (0.384 ml, 4.60 mmol) was added to the reaction mixture, which was stirred at 60° C. for 4 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 (294 mg).

Workup

  1. temperaturecooling
  2. stirringwas stirred at 60° C. for 4 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-a3560a47e8944143a6b6ebb7a6614dfc
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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