Potassium Fluoride → HCID 57917340, Verbindung

HRID 69271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69271
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[OH:25][C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1>CN1C(=O)CCC1.C(Cl)Cl.CO>[F:22][C:21]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[CH2:11][C:8]1[N:6]2[N:7]=[C:2]([N:28]3[CH2:29][CH2:30][C@H:26]([OH:25])[CH2:27]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 522689Potassium FluorideHCID 2733874(3S)-pyrrolidin-3-olHCID 581475166-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline

Produkt 1

HCID 57917340HCID 57917340, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 173.1, 100 mg, 0.316 mmol), KF (92 mg, 1.581 mmol) and (S)-3-hydroxypyrrolidine (83 mg, 0.949 mmol) were suspended in NMP (1.5 mL). The RM was stirred at 170° C. for 1 h. The mixture was diluted with DCM/MeOH (95:5) and washed with water (2×). The aqueous phases were further extracted with DCM/MeOH (95:5) (2×). The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was crystallized in DCM to afford the title compound as a beige solid (tR 2.63 min (conditions 13), MH+=364).

Aufarbeitung

  1. washwashed with water (2×)
  2. extractionThe aqueous phases were further extracted with DCM/MeOH (95:5) (2×)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was crystallized in DCM

Quellen und Nachweise

ORD-Eintrag
ord-1e26bca3add040f88e23794e2dd08034
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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