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Hydrochloric Acid → HCID 21940005, Verbindung

HRID 1242951
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1242951
Cl.[N:2]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)[CH2:6][CH2:5][CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.[C:34]1([C:43]2[CH:48]=[CH:47]C=[CH:45][CH:44]=2)[CH:39]=[CH:38][C:37](C(O)=O)=[CH:36][CH:35]=1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CN(C)C=O>[N:2]1([CH2:7][CH2:8][C:9]2[CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([NH:19][C:20]([C:21]4[CH:45]=[CH:44][C:43]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:48][CH:47]=4)=[O:22])[CH:13]=[CH:12][C:11]=3[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 21939737HCID 21939737, Verbindung

Produkt 1

HCID 21940005HCID 21940005, VerbindungAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Concentrated hydrochloric acid (2 ml) was added to N-[6-[2-(1-pyrrolidinyl)ethyl]-7,8-dihydro-2-naphthalenyl]acetamide (98.0 mg, 0.345 mmol) obtained in Reference Example 103, which was stirred at 100° C. for 16 hours. 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 (62.5 mg, 0.326 mmol) was added to a dimethylformamide solution (1.5 ml) of the resulting oily substance (79.0 mg, 0.326 mmol), [1,1′-biphenyl]-4-carboxylic acid (64.6 mg, 0.326 mmol) and DMAP (39.8 mg, 0.326 mmol) under ice-cooling, which was stirred at room temperature for 1 day. Ethyl acetate was added to the reaction mixture, washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, 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 and isopropyl ether (1:5), to give the titled compound (36.8 mg).

Aufarbeitung

  1. customobtained in Reference Example 103, 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 1 day
  9. washwashed 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)

Quellen und Nachweise

ORD-Eintrag
ord-7d9d2ed1eb884f0c8be0ead21d7c148b
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07115750B1

Notizen zur Reaktion

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