Methanesulfonic Acid → 3-amino-8-bromo-1,5-dimethyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Temperatur

40 °C

The product of Step 3 (0.831 g, 2.00 mmol) was dissolved in anhydrous anisole (16 ml) and then methanesulfonic acid (3.84 g, 40 mmol) was added in one portion. The reaction mixture was heated to 40° C. for 30 minutes with stirring, then cooled to 0° C. in an ice bath and made basic (pH=10) with concentrated ammonium hydroxide. The aqueous solution was then extracted with chloroform (3×50 ml) and the organic layers combined, dried over magnesium sulfate, filtered and concentrated to give the crude product. Purification on silica gel, eluting with 10% methyl alcohol in chloroform, providing the title compound as an XXXX (0.463 g, 82%). 1H NMR (CDCl3, 300 MHz): δ 7.32-7.23 (m, 3 H), 4.12 (d, 1 H, J=1.1 Hz), 3.27 (s, 3 H), 2.30 (d, 3 H, J=1.5 Hz) ppm.

1. temperaturecooled to 0° C. in an ice bath
2. extractionThe aqueous solution was then extracted with chloroform (3×50 ml)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give the crude product
7. customPurification on silica gel
8. washeluting with 10% methyl alcohol in chloroform

ORD-Eintrag

ord-1b16da4397874987840b76606626bd9b

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07354914B2