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

Piperazine → N-sec-butyl-5-(4-(2-fluorophenyl)-1H-imidazol-5-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 1671814
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1671814
[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([CH:15]=O)[N:9]=2)([CH2:3][CH3:4])[CH3:2].[NH4+].[OH-].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([N+:37]#[C-:38])S(C1C=CC(C)=CC=1)(=O)=O.[NH:39]1CCNCC1>C1COCC1.CCOC(C)=O>[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([C:15]1[NH:39][CH:38]=[N:37][C:26]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[F:19])[N:9]=2)([CH2:3][CH3:4])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 4837PiperazineHCID 14923Ammonium HydroxideHCID 467382311-Fluoro-2-(isocyano(tosyl)methyl)benzeneHCID 575272422-(Sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde

Produkt 1

HCID 15986167N-sec-butyl-5-(4-(2-fluorophenyl)-1H-imidazol-5-yl)thiazolo[5,4-b]pyridin-2-amineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-(sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde (presumed 0.24 mmol, 1.0 eq.) and concentrated aqueous NH4OH (0.050 mL) in THF (0.8 mL) was stirred overnight. 1-Fluoro-2-(isocyano(tosyl)methyl)benzene (0.0841 g, 0.291 mmol, 1.2 eq.) and piperazine (0.0394 g, 0.457 mmol, 1.9 eq.) were added, and the reaction mixture was stirred overnight. It was then diluted with EtOAc and washed with water, saturated aqueous NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give N-sec-butyl-5-(4-(2-fluorophenyl)-1H-imidazol-5-yl)thiazolo[5,4-b]pyridin-2-amine as a yellow solid (0.0228 g, 26% yield). LC/MS (MH)=368.23.

Aufarbeitung

  1. washwashed with water, saturated aqueous NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionMeOH was added to the residue
  6. customThe appropriate fractions were collected
  7. additionNaHCO3 (s) was added
  8. concentrationThe solution was then concentrated in vacuo not to dryness
  9. extractionextracted with CH2Cl2 (3×)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-23b9823a3df14143844e507bb23605f2
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07994337B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion