1-Methylpiperazine → 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-((4-methylpiperazin-1-yl)methyl)-4H-pyran-4-one

Methanesulfonic acid 4-oxo-5-[5-(quinazolin-4-yloxy)-pentyloxy]-4H-pyran-2-ylmethyl ester 20 (100 mg, 0.23 mmol) was dissolved in dichloromethane (3 mL). 1-Methyl-piperazine (64 μL, 0.575 mmol) was added via syringe. The mixture was stirred at 45° C. for 1 h. CH2Cl2 (50 ml) was added and the solution was washed with NaHCO3 10% (3×50 mL) and brine (3×50 mL). The product was extracted with CH2Cl2 (5×50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=99:01. 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-((4-methylpiperazin-1-yl)methyl)-4H-pyran-4-one EHT 4063 was obtained (35 mg, 35%) as a white solid.

1. washthe solution was washed with NaHCO3 10% (3×50 mL) and brine (3×50 mL)
2. extractionThe product was extracted with CH2Cl2 (5×50 mL)
3. dry with materialThe organic layer was dried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

ORD-Eintrag

ord-1115e96e1b4744a2a3330f9995a5f7da

Quelldatensatz

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07514432B2