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Triethylamine → HCID 21939737, 화합물

HRID 1242927
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HRID 1242927 반응식
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
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참가 물질

6

반응물 4

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

생성물 1

HCID 21939737HCID 21939737, 화합물수율 67.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a3560a47e8944143a6b6ebb7a6614dfc
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07115750B1

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