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Sodium hydride → 1-{2-[4-(3-Ethynyl-phenylamino)-6-(2-methoxy-ethoxy)-quinazolin-7-yloxy]-ethyl}-1H-pyridin-4-one Hydrochloride

HRID 1869096
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1869096
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6](=[O:9])[CH2:5][CH:4]=1.Cl.[Cl:11][CH2:12][CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[CH:33])[CH:27]=3)=[N:20][CH:21]=[N:22]2)=[CH:17][C:16]=1[O:34][CH2:35][CH2:36][O:37][CH3:38]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[ClH:11].[C:32]([C:28]1[CH:27]=[C:26]([NH:25][C:19]2[C:18]3[C:23](=[CH:24][C:15]([O:14][CH2:13][CH2:12][N:3]4[CH:4]=[CH:5][C:6](=[O:9])[CH:7]=[CH:8]4)=[C:16]([O:34][CH2:35][CH2:36][O:37][CH3:38])[CH:17]=3)[N:22]=[CH:21][N:20]=2)[CH:31]=[CH:30][CH:29]=1)#[CH:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydride2×HCID 17984897Piridin-4-one2×HCID 18925049[7-(2-Chloro-ethoxy)-6-(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)-amine Hydrochloride

Produkt 1

HCID 189250871-{2-[4-(3-Ethynyl-phenylamino)-6-(2-methoxy-ethoxy)-quinazolin-7-yloxy]-ethyl}-1H-pyridin-4-one HydrochlorideAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

NaH (30 mg of 60% in mineral oil, 0.77 mmol) was added to anhydrous DMF (2.0 mL) followed by pyrid-4-one (79 mg, 0.83 mmol). The mixture was stirred 40 minutes at 22° C. until all solids dissolved and the evolution of H2 ceased. The title product of Example 34 (120 mg, 0.28 mmol) and tetrabutylammonium iodide (15 mg) were added and the reaction mixture was stirred at 22° C. for 7 days under N2. Additional pyrid-4-one (79 mg) and NaH (30 mg of 60%) were dissolved in DMF (2 mL) and the solution was added to the reaction mixture. After another 4 days stirring the mixture was partitioned between CHCl3 and brine. The organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica utilizing 10% methanol/CH2Cl2 to afford 65 mg of the free base of the title product which was converted to the mono-hydrochloride salt according to the procedure described for Example 28 (66 mg; M.P. 240°-248° C. (dec); LC-MS: 457 (MH+); anal. RP-HPLC RT: 3.23 min)

Aufarbeitung

  1. dissolutiondissolved
  2. stirringthe reaction mixture was stirred at 22° C. for 7 days under N2
  3. additionthe solution was added to the reaction mixture
  4. stirringAfter another 4 days stirring the mixture
  5. customwas partitioned between CHCl3 and brine
  6. dry with materialThe organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica utilizing 10% methanol/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e36ecee2a96c402ebcac4c3322e8b145
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE041065E1

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