Ammonium Chloride → 1-(4-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)phenyl)ethanol

HRID 454930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454930
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([O:15][C:16]2[C:17]([C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][CH:23]=3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12]1.[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[Cl-].[NH4+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:12][CH:13]([O:15][C:16]2[C:17]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([OH:30])[CH3:29])=[CH:24][CH:23]=3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:14]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 585478541-(4-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)phenyl)ethanoneHCID 131720822Sodium tetraborohydride

Produkt 1

HCID 585480711-(4-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)phenyl)ethanolAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(4-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)phenyl)ethanone (see EXAMPLE 10.26; 99 mg, 0.25 mmol) was dissolved in 10 ml of methanol. This solution was cooled down to 0° C. using an ice bath and sodium tetraborohydride (19 mg, 0.50 mmol) was added in portions. The reaction mixture was stirred for 4 hours at ambient temperature, and then saturated aqueous solution of ammonium chloride (5 mL) was added. The methanol was evaporated off under reduced pressure then the reaction mixture was taken up in ethyl acetate. The organic layer was separated from the aqueous layer. This extraction was repeated one more time and then the organic layers were combined and dried over magnesium sulphate, followed by concentrating under reduced pressure. The residue was purified by column chromatography on silica gel to give (racemic mixture) 1-(4-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)phenyl)ethanol (75 mg, 0.19 mmol, 75% yield). ESI-MS (M+1): 399 calc. for C24H22N4O2 398.

Aufarbeitung

  1. customThe methanol was evaporated off under reduced pressure
  2. customThe organic layer was separated from the aqueous layer
  3. extractionThis extraction
  4. dry with materialdried over magnesium sulphate
  5. concentrationby concentrating under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c00d7bccf6594ef5a8b90daa7353be35
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497265B2

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