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

Sodium hydride → N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594165
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 594165
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][N:26]=2)[CH:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+]>CS(C)=O>[CH:31]([C:28]1[CH:29]=[CH:30][C:25]([N:19]([CH:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])[S:16]([C:13]2[CH:12]=[CH:11][C:10]([O:8][CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:15][CH:14]=2)(=[O:17])=[O:18])=[N:26][CH:27]=1)([CH3:33])[CH3:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 2773573(Oxan-4-yl)methanol2×HCID 898762524-fluoro-N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)benzenesulfonamide

Produkt 1

HCID 72194692N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamideAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of (tetrahydro-2H-pyran-4-yl)methanol (10.20 mg, 0.088 mmol) and 4-fluoro-N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)benzenesulfonamide (32 mg, 0.088 mmol) in dimethyl sulfoxide (DMSO) (1 mL) stirred in air at room temperature was added sodium hydride (3.51 mg, 0.088 mmol, 60% wt in mineral oil). The reaction mixture was stirred at 20° C. for 2 hours. Additional (tetrahydro-2H-pyran-4-yl)methanol (10.20 mg, 0.088 mmol) and sodium hydride (3.51 mg, 0.088 mmol, 60% wt in mineral oil) were added and the reaction mixture stirred overnight. The reaction was carefully quenched with isopropanol (1 mL) and water (1 mL). The solvent was evaporated in vacuo and the residue partitioned between water (5 mL) and dichloromethane (2×5 mL), then separated using a hydrophobic frit. The solvent was removed in vacuo and the crude was purified by mass directed autoprep (formic acid modifier) to give the title product (32 mg). LCMS (2 min, formic) Rt 1.41 min, m/z (ES+) 461 (M+H).

Aufarbeitung

  1. stirringthe reaction mixture stirred overnight
  2. customThe reaction was carefully quenched with isopropanol (1 mL) and water (1 mL)
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between water (5 mL) and dichloromethane (2×5 mL)
  5. customseparated
  6. customThe solvent was removed in vacuo
  7. customthe crude was purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-8785bb45fb514abf87f805e99869b103
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242972B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion