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Ammonium Chloride → HCID 178428856, Verbindung

HRID 384498
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384498
[CH3:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]=1[CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=1)[C:14]#[N:15].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][C:2]1[C:7](=[O:8])[C:6]2[C:5](=[CH:1][CH:2]=[CH:3][CH:9]=2)[NH:4][C:3]=1[CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:14]2[NH:29][N:28]=[N:27][N:15]=2)[CH:16]=[C:17]([O:19][CH2:20][CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 685083823-[(3-methyl-4-oxo-1,4-dihydropyridin-2-yl)methoxy]-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzonitrile

Produkt 1

HCID 178428856HCID 178428856, VerbindungAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-[(3-methyl-4-oxo-1,4-dihydropyridin-2-yl)methoxy]-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzonitrile (100 mg) in DMF (2 mL) were added sodium azide (18 mg) and ammonium chloride (15 mg), followed by stirring at 100° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a 1M aqueous sodium hydroxide solution and washed with diethyl ether. The aqueous layer was adjusted to a pH of 2 by adding 1M hydrochloric acid, followed by extraction with chloroform and a mixed solvent of chloroform-methanol (5:1). The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by thin layer chromatography (developer: chloroform/methanol=6/1) and washed with ethyl acetate to obtain 3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)-5-(1H-tetrazol-5-yl)phenoxy]methyl}quinolin-4(1H)-one (37 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a 1M aqueous sodium hydroxide solution
  3. washwashed with diethyl ether
  4. additionby adding 1M hydrochloric acid
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by thin layer chromatography (developer: chloroform/methanol=6/1)
  10. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4cfb4f836b0c4993b823b6a1cfaa8241
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367702B2

Notizen zur Reaktion

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