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

Lithium hexamethyldisilazane → HCID 86687709, Verbindung

HRID 1473639
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473639
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][C:9]2[N:10]=[CH:11][S:12][CH:13]=2)=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].F[C:27]1[C:36]2[C:31](=[C:32](F)[C:33](F)=[C:34]([S:38]([O-])(=[O:40])=[O:39])[C:35]=2F)[C:30]([Cl:44])=[N:29][C:28]=1C1C(F)=C(F)C(F)=C(F)C=1F>C1COCC1>[Cl:44][C:30]1[C:31]2[C:36](=[CH:35][C:34]([S:38]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=3)[C:9]3[N:10]=[CH:11][S:12][CH:13]=3)(=[O:40])=[O:39])=[CH:33][CH:32]=2)[CH:27]=[CH:28][N:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2733832Lithium hexamethyldisilazaneHCID 86687708N-[(4-methoxyphenyl)methyl]-1,3-thiazol-4-amineHCID 86687710HCID 86687710, Verbindung

Produkt 1

HCID 86687709HCID 86687709, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-4-amine (Intermediate PPPPP; 0.085 g, 0.384 mmol) in THF (1.408 ml) was added lithium bis(trimethylsilyl)amide (0.403 ml, 0.403 mmol) drop wise over 10 min. The mixture was stirred for 15 minutes prior to the addition of a solution of perfluorophenyl-1-chloroisoquinoline-6-sulfonate (From Step 1 in Example 73; 0.15 g, 0.366 mmol) in THF (1.0 ml). After 45 minutes of stirring (ice melt) LCMS indicated that the reaction was nearly complete. The mixture was allowed to stir and slowly warm to room temperature overnight. LCMS indicated that the reaction was complete. The reaction was quenched by the addition of acetic acid (˜2 ml) and the resulting mixture was dried under reduced pressure and purified via silica gel chromatography (40 g silicycle HP column) ramping EtOAc in heptane (0-50%) providing product 1-chloro-N-(4-methoxybenzyl)-N-(thiazol-4-yl)isoquinoline-6-sulfonamide. m/z (ESI) 446.1 (M+H)+.

Aufarbeitung

  1. additionTo a flask containing
  2. stirringAfter 45 minutes of stirring (ice melt) LCMS
  3. stirringto stir
  4. customThe reaction was quenched by the addition of acetic acid (˜2 ml)
  5. customthe resulting mixture was dried under reduced pressure
  6. custompurified via silica gel chromatography (40 g silicycle HP column)

Quellen und Nachweise

ORD-Eintrag
ord-e384ac51022742b7bc2493244a53f027
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012443B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion