Hydrochloric Acid → 1-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1892378

Reaktionsgleichung

Reaktionsgleichung von HRID 1892378
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[N:11]=1)=[CH2:5])C.Cl.C([O-])(O)=O.[Na+]>CO>[N:22]1[C:23]2[C:18](=[CH:17][C:16]([CH2:15][C:12]3[N:10]4[N:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]4=[N:14][N:13]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 698109446-((6-(1-Ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

Produkt 1

HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanoneAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-((6-(1-ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline in MeOH (30 mL) was added excess 3N HCl solution. The solution was stirred at rt overnight and neutralized with saturated NaHCO3 solution. Organic solvent was evaporated and the residue was extracted with EtOAc three times. Organic layers were combined, washed with brine and dried over Na2SO4. Solvent was evaporated and the crude was purified by column chromatography (DCM:MeOH=95:5) to give the title compound as yellow solid (51.3%). LCMS (method B): [MH]+=304.1, tR=1.708 min.

Aufarbeitung

  1. customOrganic solvent was evaporated
  2. extractionthe residue was extracted with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customthe crude was purified by column chromatography (DCM:MeOH=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-120df94ca1a6475b9dcd57d6034c247b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507676B2

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