Hydrochloric Acid → 6-[6-(1-Azetidin-3-yl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-fluoro-quinoline

HRID 69184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69184
O1CCOCC1.C(OC([N:14]1[CH2:17][CH:16]([N:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][C:26]4[N:27]([C:29]([CH2:32][C:33]5[CH:34]=[C:35]6[C:40](=[CH:41][C:42]=5[F:43])[N:39]=[CH:38][CH:37]=[CH:36]6)=[CH:30][N:31]=4)[N:28]=3)[CH:20]=[N:19]2)[CH2:15]1)=O)(C)(C)C.Cl>CCOC(C)=O.C([O-])(O)=O.[Na+]>[NH:14]1[CH2:15][CH:16]([N:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][C:26]4[N:27]([C:29]([CH2:32][C:33]5[CH:34]=[C:35]6[C:40](=[CH:41][C:42]=5[F:43])[N:39]=[CH:38][CH:37]=[CH:36]6)=[CH:30][N:31]=4)[N:28]=3)[CH:20]=[N:19]2)[CH2:17]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 686331183-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-azetidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 686314996-[6-(1-Azetidin-3-yl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-fluoro-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86584982Sodium bicarbonate ethyl acetateLösungsmittel

Versuchsvorschrift

Dioxane (5 mL) was charged in a flask. 3-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-azetidine-1-carboxylic acid tert-butyl ester (Stage 146.2, 100 mg, 0.200 mmol) and HCl in dioxane (4 M solution, 500 μL, 2.002 mmol) were then added and the mixture was stirred at rt for 1 h. The RM was diluted with EtOAc/NaHCO3. The organic layer was separated and washed with brine (2×) then dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep® silica gel column, DCM/(DCM/MeOH 19:1)=100:0→0:100) and precipitated in Et2O to afford the title compound as a foam (tR 2.87 min (conditions 3), MH+=400.1).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine (2×)
  3. dry with materialthen dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (CombiFlash® Companion System®
  7. customwith a 4 g RediSep® silica gel column, DCM/(DCM/MeOH 19:1)=100:0→0:100) and precipitated in Et2O

Quellen und Nachweise

ORD-Eintrag
ord-0261fe5d6eff4e71b3ee612489c53096
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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