Potassium Iodide → 4-Ethoxy-7-[2-[1-(6-methylpyridazin-3-yl)-4-piperidyl]ethoxy]quinazoline

HRID 624103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624103
Cl[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1.[OH:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:16][C:13]1[N:12]=[N:11][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][O:17][C:18]3[CH:27]=[C:26]4[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]4)=[CH:20][CH:19]=3)[CH2:5][CH2:6]2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 149892183-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazineHCID 1358487477-Hydroxy-4-ethoxyquinazoline

Produkt 1

HCID 5044704-Ethoxy-7-[2-[1-(6-methylpyridazin-3-yl)-4-piperidyl]ethoxy]quinazolineAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine (76 mg, 318 μmol), 7-hydroxy-4-ethoxyquinazoline (100 mg, 526 mmol), potassium carbonate (109 mg, 789 mmol) and potassium iodide (53 mg, 319 mmol) in DMF (5 mL) was heated at 90° C. overnight in an argon atmosphere. The mixture was concentrated, and the residue partitioned between ethyl acetate (100 mL), and water (20 mL). The organic phase was dried (MgSO4), filtered, concentrated and purified by column chromatography (silica), using gradient elution (ethyl acetate-methanol/EA). The combined fractions gave a white solid (22 mg, 18%). The 1H nmr data are recorded in Table 6 below.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between ethyl acetate (100 mL), and water (20 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica)
  7. washelution (ethyl acetate-methanol/EA)

Quellen und Nachweise

ORD-Eintrag
ord-2df3f614c09b44bbb766e9594385b2f0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303026B2

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