StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Boron trifluoride etherate → 5-[4-Fluoro-3-(morpholinomethyl)phenyl]-3-(1-isopropyltriazol-4-yl)pyridin-2-amine

HRID 1053137
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1053137
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([F:22])=[C:12]([C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=O)[CH:13]=2)=[CH:4][C:3]=1[C:23]1[N:24]=[N:25][N:26]([CH:28]([CH3:30])[CH3:29])[CH:27]=1.B(F)(F)F.CCOCC.[BH4-].[Na+]>C1COCC1>[F:22][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[C:3]([C:23]3[N:24]=[N:25][N:26]([CH:28]([CH3:29])[CH3:30])[CH:27]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)=[CH:13][C:12]=1[CH2:14][N:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 90273335[5-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-fluoro-phenyl]-morpholino-methanone

Produkt 1

HCID 771063665-[4-Fluoro-3-(morpholinomethyl)phenyl]-3-(1-isopropyltriazol-4-yl)pyridin-2-amineAusbeute 41,66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of [5-[6-amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-fluoro-phenyl]-morpholino-methanone (150 mg, 0.365 mmol) in THF (10.0 mL) was added BF3.Et2O (0.25 mL, 1.827 mmol) at 0° C. and stirred for 30 min. After 30 min, NaBH4 (69 mg, 1.827 mmol) was added at 0° C. and stirred at room temperature for 18 h. After cooling to 0° C., quenched with MeOH (2 mL) and heated to reflux for 6 h. The reaction mixture was diluted with EtOAc (20 mL), washed with water (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. Crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 5% MeOH in DCM to afford 60 mg (yield: 41.66%) of the title compound as white solid.

Aufarbeitung

  1. waitAfter 30 min
  2. stirringstirred at room temperature for 18 h
  3. customquenched with MeOH (2 mL)
  4. temperatureheated
  5. temperatureto reflux for 6 h
  6. additionThe reaction mixture was diluted with EtOAc (20 mL)
  7. washwashed with water (20 mL)
  8. dry with materialdried over anhydrous Na2SO4 and solvent
  9. customwas evaporated under reduced pressure
  10. customCrude compound was purified by column
  11. washThe column was eluted with 5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-3468793a45514c0bb69c1ed0becfbbc6
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09393248B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion