p-Toluenesulfonic acid → 2-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one

Temperature

150 °C

To a mixture of 2-aminobenzamide (1.0 g, 7.35 mmol) and 4-(4-acetylpiperazin-1-yl)benzaldehyde (1.71 g, 7.35 mmol) in DMA (60 mL) was added p-TsOH (0.140 g, 0.73 mmol) and NaHSO3 (0.841 g, 8.1 mmol). The reaction mixture was heated at 150° C. for 21 hours, concentrated to half-volume, diluted with water (300 mL), extracted with CH2Cl2 (2×200 mL), washed with brine (200 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with 100% CH2Cl2 to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH), to afford 2-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one as a yellow solid (2.27 g, 89%).

1. concentrationconcentrated to half-volume
2. additiondiluted with water (300 mL)
3. extractionextracted with CH2Cl2 (2×200 mL)
4. washwashed with brine (200 mL)
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography
9. washeluting with 100% CH2Cl2 to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH)

ORD record

ord-10d89f78bb49442ea62802f98ed57985

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2