3,4-bis(Benzyloxy)-6-{2-[5-(trifluoromethyl)pyridin-3-yl]ethynyl}pyridazine → HCID 178518838, compound

3,4-bis(Benzyloxy)-6-{2-[5-(trifluoromethyl)pyridin-3-yl]ethynyl}pyridazine (Intermediate 31; 1.5 g, 3.25 mmol) was dissolved in methanol (10 mL) and 10% palladium on carbon (0.04 g) was added before the mixture was purged and subjected to hydrogen gas. The reaction mixture was stirred for 30 min at room temperature under a hydrogen atmosphere. The reaction mass was then filtered through a celite bed under nitrogen atmosphere and washed with methanol. The filtrate was concentrated in vacuo before the crude was re-dissolved in methanol (10 mL) and 10% palladium on carbon (0.04 g) was added before the mixture was purged and subjected to a pressure of hydrogen gas (200 psi), stirring at room temperature overnight. Upon completion the resulting mixture was filtered through celite under nitrogen and washed with methanol. The filtrate was concentrated under vacuum to afford the crude compound (0.2 g) which was then purified by the preparative HPLC to yield 4-hydroxy-6-(2-(5-(trifluoromethyl)pyridin-3-yl)ethyl)pyridazin-3(2H)-one (0.03 g, 82% yield).

1. customwas purged
2. filtrationThe reaction mass was then filtered through a celite bed under nitrogen atmosphere
3. washwashed with methanol
4. concentrationThe filtrate was concentrated in vacuo before the crude
5. dissolutionwas re-dissolved in methanol (10 mL)
6. addition10% palladium on carbon (0.04 g) was added before the mixture
7. customwas purged
8. stirringstirring at room temperature overnight
9. filtrationUpon completion the resulting mixture was filtered through celite under nitrogen
10. washwashed with methanol
11. concentrationThe filtrate was concentrated under vacuum
12. customto afford the crude compound (0.2 g) which
13. customwas then purified by the preparative HPLC

ORD record

ord-9da914f925fc4af7b31e634a3becf03c

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290456B2