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Hydrochloric Acid → HCID 21939720, 화합물

HRID 1242954
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HRID 1242954 반응식
Cl.[CH3:2][N:3]([CH3:20])[CH2:4][CH2:5][C:6]1[CH2:15][CH2:14][C:13]2[CH:12]=[C:11]([NH:16][C:17](=[O:19])[CH3:18])[CH:10]=[CH:9][C:8]=2[CH:7]=1.CCN=C=NCCCN(C)C.[C:32]1([C:41]2[CH:46]=[CH:45]C=[CH:43][CH:42]=2)[CH:37]=[CH:36][C:35](C(O)=O)=[CH:34][CH:33]=1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CN(C)C=O>[CH3:20][N:3]([CH3:2])[CH2:4][CH2:5][C:6]1[CH2:15][CH2:14][C:13]2[CH:12]=[C:11]([NH:16][C:17]([C:18]3[CH:43]=[CH:42][C:41]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:46][CH:45]=3)=[O:19])[CH:10]=[CH:9][C:8]=2[CH:7]=1
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 21939837HCID 21939837, 화합물

생성물 1

HCID 21939720HCID 21939720, 화합물수율 22.5%

시약·촉매·용매 3

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Concentrated hydrochloric acid (1.5 ml) was added to N-[6-[2-(dimethylamino)ethyl]-7,8-dihydro-2-naphthalenyl]acetamide (57.5 mg, 0.223 mmol) obtained in Reference Example 104, which was stirred at 100° C. for 1 hour. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. WSC (29.2 mg, 0.139 mmol) was added to a dimethylformamide solution (0.7 ml) of the resulting oily substance (30 mg, 0.139 mmol), [1,1′-biphenyl]-4-carboxylic acid (30.2 mg, 0.139 mmol) and DMAP (16.9 mg, 0.139 mmol) under ice-cooling, which was stirred at room temperature for 16 hours. Ethyl acetate was added to the reaction mixture, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting residue was purified by aluminum column chromatography (development solvent; ethyl acetate), powdered with ethyl acetate-isopropyl ether (1:5), to give the titled compound (12.4 mg).

후처리

  1. customobtained in Reference Example 104, which
  2. distillationThe solvent was distilled out under reduced pressure
  3. additionEthyl acetate was added to the residue, which
  4. washwas washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled out under reduced pressure
  7. temperaturecooling
  8. stirringwhich was stirred at room temperature for 16 hours
  9. washwas washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled out under reduced pressure
  12. customThe resulting residue was purified by aluminum column chromatography (development solvent; ethyl acetate)

출처 및 근거

ORD 기록
ord-8e3fd3392ccc4c34aceea08b09454f9a
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07115750B1

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