Reaktion #805755

Reaktionsgleichung

HCl

Compound 6a

(E)-Methyl 2-hydroxy-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

LiOH

water

→

title compound 63

(E)-2-Hydroxy-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoic acid

Lösungsmittel

THF MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to rt
2. 2
   ExtraktionThe reaction mixture was then extracted with 20% MeOH in DCM (4×200 mL)
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

Compound 6a (80 mg, 0.16 mmol) was suspended in THF/MeOH (1:1 v/v, 8 mL) and treated with 1 N LiOH solution (0.8 mL, 0.8 mmol). The mixture was stirred at 90° C. for 30 min, allowed to cool to rt, and treated with water (20 mL). The pH of the mixture was adjusted to ca. pH 3 using 1 N HCl solution. The reaction mixture was then extracted with 20% MeOH in DCM (4×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the title compound 63 as an orange solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.60 (br. s., 1H), 8.55-8.67 (m, 1H), 8.20 (d, J=5.6 Hz, 1H), 8.12-8.18 (m, 1H), 8.04-8.12 (m, 2H), 8.00 (d, J=8.1 Hz, 1H), 7.88 (m, 3H), 7.69 (br. s., 1H), 7.37 (d, J=1.2 Hz, 1H), 7.31 (d, J=8.3 Hz, 1H), 6.49 (d, J=5.9 Hz, 1H), 4.10 (m 4H), 3.88 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H23N5O4: 494.2 (M+H). Found 494.4.

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