Hydrochloric Acid → HCID 178440499, Verbindung

HRID 646040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646040
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:32]#[N:33])=[CH:27][CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:34]([CH3:36])[CH3:35])[O:11][N:10]=1.[Cl-].[NH4+].[N-:39]=[N+:40]=[N-:41].[Na+].Cl>CN(C)C=O.O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:32]3[NH:41][N:40]=[N:39][N:33]=3)=[CH:27][CH:26]=[CH:25]4)=[CH:20][CH:21]=2)=[C:12]([CH:34]([CH3:36])[CH3:35])[O:11][N:10]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 247393306-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarbonitrile

Produkt 1

HCID 178440499HCID 178440499, VerbindungAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarbonitrile (75 mg, 0.14 mmol) in dimethylformamide (1 mL) was added ammonium chloride (8.5 mg, 0.15 mmol) and sodium azide (10 mg, 0.15 mmol). The mixture was then heated to 100° C. for 18 hours. The reaction was diluted with water (5 mL) and acidified with 2 N HCl (2 mL). A white precipitate was formed upon acidification which was removed via filtration and dried under high vacuum for four hours. The crude residue was then dissolved in methanol (5 mL) and purified via preparative high pressure liquid chromatography (C18 Luna column eluted with a 10-100% gradient of acetonitrile in water with 0.1% formic acid modifier) to give the title compound as a white solid (62 mg, 78%) 1H NMR (CDCl3): δ 8.54 (d, J=9 Hz, 1H), 7.91-8.02 (m, 2H), 7.75 (d, J=9 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.54 (dd, J=2, 8 Hz, 1H), 7.60-7.48 (m, 3H) 7.38 (d, J=9 Hz, 2H), 7.34-7.27 (m, 1H), 6.88 (d, J=9 Hz, 2H), 4.78 (s, 2H), 3.42-3.28 (m, 1H), 1.53-1.34 (m, 6H). ESI-LCMS m/z 556 (M+H)+.

Aufarbeitung

  1. customA white precipitate was formed upon acidification which
  2. customwas removed via filtration
  3. customdried under high vacuum for four hours
  4. dissolutionThe crude residue was then dissolved in methanol (5 mL)
  5. custompurified via preparative high pressure liquid chromatography (C18 Luna column
  6. washeluted with a 10-100% gradient of acetonitrile in water with 0.1% formic acid modifier)

Quellen und Nachweise

ORD-Eintrag
ord-5f4b5be72e8b4e9196c0394093c9bf8c
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705028B2

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