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Hydrochloric Acid → 1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-2,2,2-trifluoro-1-(quinolin-6-yl)ethanol

HRID 69275
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 69275
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[F:23][C:24]([Si](C)(C)C)([F:26])[F:25].[F-].[K+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)([OH:12])[C:24]([F:26])([F:25])[F:23])=[CH:9][N:10]=2)[N:7]=1
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

Produkt 1

HCID 866351161-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-2,2,2-trifluoro-1-(quinolin-6-yl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanone (Stage 1.2, 50 mg, 0.162 mmol) was dissolved in DMF (5 mL) and (trifluoromethyl)trimethylsilane (1.294 mL, 8.10 mmol) and KF (4.70 mg, 0.081 mmol) were introduced. After 30 min at rt, 1 N HCl was added to the RM. It was stirred at rt for 20 h. the reaction was not completed. It was then heated at 150° C. under microwave irradiations for 5 min. It was extracted with EtOAc twice. Combined organic layers was washed with brine and dried over Na2SO4. It was filtered and the solvent was removed to afford as brown solid 1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-2,2,2-trifluoro-1-(quinolin-6-yl)ethanol (tR 0.8 min (conditions 2), MH+=379).

Aufarbeitung

  1. temperatureIt was then heated at 150° C. under microwave irradiations for 5 min
  2. extractionIt was extracted with EtOAc twice
  3. washCombined organic layers was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationIt was filtered
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-b348cfc2f0864184af2134e181030c88
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822468B2

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