Hydrochloric Acid → 2-{4-[3-(4,6-Difluoro-1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-ethanol

HRID 69288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69288
[F:1][C:2]1[C:10]([CH2:11][C:12]2[N:16]3[N:17]=[C:18]([C:21]4[CH:22]=[N:23][N:24]([CH2:26][CH2:27][O:28]C5CCCCO5)[CH:25]=4)[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[C:9]([F:35])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:36].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[F:1][C:2]1[C:10]([CH2:11][C:12]2[N:16]3[N:17]=[C:18]([C:21]4[CH:22]=[N:23][N:24]([CH2:26][CH2:27][OH:28])[CH:25]=4)[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[C:9]([F:35])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:36]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 686334013-(4,6-difluoro-1-methyl-1H-indazol-5-ylmethyl)-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazine

Produkt 1

HCID 579174392-{4-[3-(4,6-Difluoro-1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(4,6-difluoro-1-methyl-1H-indazol-5-ylmethyl)-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazine (Stage 285.1, 30 mg, 0.061 mmol) in dioxane (2 mL) stirred at 0° C. was added a solution of HCl in dioxane (4 M, 0.152 mL). The RM was stirred 1 h at rt, poured in a solution 10% NaHCO3, and the aqueous phase was extracted with DCM. The combined organic phases were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, hexane/EtOAc=100:0->80:20) to afford the title compound as a white powder (tR 3.68 min (conditions 3), MH+=410.2, 1H-NMR in DMSO-d6: 8.38 (s, 1H); 8.19 (s, 1H); 8.06 (s, 1H); 8.04 (d, 1H); 7.53-7.46 (m, 3H); 4.97 (t, 1H); 4.40 (s, 2H); 4.18 (t, 2H); 3.97 (s, 3H); 3.76 (q, 2H)).

Aufarbeitung

  1. extractionthe aqueous phase was extracted with DCM
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, hexane/EtOAc=100:0->80:20)

Quellen und Nachweise

ORD-Eintrag
ord-963ee83d76b84ab98a1e10dbab706db1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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