Potassium Hydroxide → HCID 11712061, Verbindung

KOH (0.089 g, 1.59 mmol) was added to a solution of dicyclopropyl(5-mercapto-1,3,4-thiadiazol-2-yl)methanol (0.363 g, 1.60 mmol) in dry MeOH. When a solution was obtained, the reaction mixture was concentrated to dryness. Dry toluene was then added and the mixture was concentrated to dryness again. The residue was dissolved in NMP, 7-bromo-4-pyridin-3-yl-2H-chromen-2-one (400 mg, 1.32 mmol) was added and the resulting mixture was stirred at 120° C. for 16 h. The reaction mixture was cooled and partitioned between aqueous NH4OAc and EtOAc. The organic phase was washed with brine, dried over anhydrous Na2SO4, concentrated and purified on silica gel column (toluene-acetone, 90:10 to 70:30) to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.82 (d, 1H), 8.72 (s,1H), 7.81 (dt, 1H), 7.64 (s, 1H), 7.58-7.50 (m, 1H), 7.48-7.41 (m, 2H), 6.46 (s, 1H), 2.57 (s, 1H), 1.40-1.31 (m, 2H), 0.69-0.57 (m, 6H), 0.50-0.44 (m, 1H).

1. customWhen a solution was obtained
2. concentrationthe reaction mixture was concentrated to dryness
3. additionDry toluene was then added
4. concentrationthe mixture was concentrated to dryness again
5. dissolutionThe residue was dissolved in NMP
6. temperatureThe reaction mixture was cooled
7. custompartitioned between aqueous NH4OAc and EtOAc
8. washThe organic phase was washed with brine
9. dry with materialdried over anhydrous Na2SO4
10. concentrationconcentrated
11. custompurified on silica gel column (toluene-acetone, 90:10 to 70:30)

ORD-Eintrag

ord-7e68e81e8e2349f48e35e86ae4e10d44

Quelldatensatz

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07553973B2