Triethylamine → 4-[4-(Hydroxyaminocarbonyl)methoxy-3,5-dimethyphenyl]-2-methyl-1(2H)phthalazinone

A solution of example 108 (1.15 g) in dichloromethane (30 ml) at 0° C. was treated with triethylamine (0.52 g) followed by isopropenyl chloroformate (0.41 g), and the mixture was stirred for 1 h. O-tert-butyldimethylsilylhydroxylamine (0.50 g) was then added and the mixture was stirred for a further 18 h. The reaction mixture was washed with 10% citric acid (20 ml), saturated sodium bicarbonate (20 ml) and the concentrated to dryness in vacuo. A solution of the residual solid in tetrahydrofuran (30 ml) and water (5 ml) was then treated with a 1.0 M solution of tetrabutylammonium fluoride in tetahydrofuran (1 ml) and stirred 1 h the resultant crude mixture was concentrated on to silica and purified by chromatography, eluting with 5% methanol in dichloromethane, to provide the title compound as a white solid (0.10 g).

1. stirringthe mixture was stirred for a further 18 h
2. washThe reaction mixture was washed with 10% citric acid (20 ml), saturated sodium bicarbonate (20 ml)
3. concentrationthe concentrated to dryness in vacuo
4. additionA solution of the residual solid in tetrahydrofuran (30 ml) and water (5 ml) was then treated with a 1.0 M solution of tetrabutylammonium fluoride in tetahydrofuran (1 ml)
5. stirringstirred 1 h the resultant crude mixture
6. concentrationwas concentrated on to silica
7. custompurified by chromatography
8. washeluting with 5% methanol in dichloromethane

ORD-Eintrag

ord-a7fad0d52b764d34b4897ee33808c147

Quelldatensatz

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06118001