Hydrate;hydrochloride → 8-Chloro-2-(4-isopropyl-thiazol-2-yl)-7-(2-morpholin-4-yl-ethoxy)-quinolin-4-ol

HRID 1422532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422532
[Cl:1][C:2]1[C:3]([O:21][CH2:22][CH:23](OC)OC)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[OH:20].Cl.[OH2:29]>CC(O)=O>[Cl:1][C:2]1[C:3]([O:21][CH2:22][CH2:23][N:10]2[CH2:11][CH2:2][O:29][CH2:8][CH2:9]2)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:18])[CH3:19])[N:16]=1)[CH:8]=[C:7]2[OH:20]

Komponenten

4

Edukt 2

HCID 21885828Hydrate;hydrochlorideHCID 178496099HCID 178496099, Verbindung

Produkt 1

HCID 1784398028-Chloro-2-(4-isopropyl-thiazol-2-yl)-7-(2-morpholin-4-yl-ethoxy)-quinolin-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

8-Chloro-7-(2,2-dimethoxy-ethoxy)-2-(4-isopropyl-thiazol-2-yl)-quinolin-4-ol (5.0 g, 12.3 mmol) was dissolved in HOAc (100 mL) and 1.4 N HCl/H2O (50 mL). The reaction mixture was heated to 60° C. with stirring for 2 hrs. After cooled back to room temperature and concentrated, the residue was co-evaporated with toluene (2×50 mL). Then the crude was dissolved in DCM (100 mL) and cooled to 0° C. with stirring. Morphiline (1.6 g, 18.4 mmol) and NaHB(OAc)3 (3.9 g, 18.4 mmol) were added to the reaction mixture. After stirring at room temperature for 1 h, the reaction mixture was washed with sat. NaHCO3, brine and dried by Na2SO4. After concentration, the crude was purified by silica gel chromatography to afford 5.0 g of 8-chloro-2-(4-isopropyl-thiazol-2-yl)-7-(2-morpholin-4-yl-ethoxy)-quinolin-4-ol as a white solid.

Aufarbeitung

  1. temperatureAfter cooled back to room temperature
  2. concentrationconcentrated
  3. dissolutionThen the crude was dissolved in DCM (100 mL)
  4. temperaturecooled to 0° C.
  5. stirringwith stirring
  6. stirringAfter stirring at room temperature for 1 h
  7. washthe reaction mixture was washed with sat. NaHCO3, brine
  8. dry with materialdried by Na2SO4
  9. concentrationAfter concentration
  10. customthe crude was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-81da5162534242298dab728203f48977
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927484B2

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