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

Water → 1-(4,6-Di-pyridin-3-yl-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-urea

HRID 447067
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 447067
Br[C:2]1[C:7]2[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=2[CH:5]=[C:4](Br)[N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:2]2[C:7]3[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=3[CH:5]=[C:4]([C:7]3[CH:2]=[N:3][CH:4]=[CH:5][CH:6]=3)[N:3]=2)[CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 580332371-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

Produkt 1

HCID 426229601-(4,6-Di-pyridin-3-yl-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-ureaAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-(4,6-dibromo-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-urea (0.07 g, 0.17 mmol) in DMF:H2O (3:1, 4 mL) was added pyridine-3-boronic acid (0.08 g, 0.68 mmol) and potassium phosphate tribasic (0.09 g, 0.43 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was degassed by bubbling nitrogen for 15-20 min followed by addition of Pd(PPh3)4 (0.04 g, 0.07 mmol). The resulting solution was again degassed for 15-20 min followed by heating up to 90° C. overnight. After completion of reaction (TLC monitoring), the reaction mixture was cooled, water was added and extracted with ethyl acetate, dried over Na2SO4 and evaporated to dryness under high vacuum. The crude residue was purified by Prep HPLC to get the desired product (0.015 g, 23%).

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen for 15-20 min
  3. customThe resulting solution was again degassed for 15-20 min
  4. customAfter completion of reaction (TLC monitoring)
  5. temperaturethe reaction mixture was cooled
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness under high vacuum
  9. customThe crude residue was purified by Prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-af33ba7c571440c392724a530bbac7e4
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481544B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion