Lithium Hydroxide → HCID 44476487, Verbindung

A mixture of 3-pyrrolidinecarboxylic acid (ABCR Product List; 36.0 mg, 0.312 mmol), and sodium hydride (60%; 9.99 mg, 0.250 mmol) in dimethyl sulfoxide (DMSO) (2 ml) were stirred at room temperature for 30 min. 1-Chloro-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D7; 50 mg, 0.125 mmol) was added and the reaction mixture was left to stir at 120° C. under nitrogen for 3 hours. The cooled reaction mixture was loaded onto an SCX column. The column was flushed with methanol and then the desired product was eluted with 2M ammonia in methanol. The solvent was removed in vacuo from the appropriate fractions to give a yellow solid. Lithium hydroxide (2.99 mg, 0.125 mmol), methanol (2.00 ml), water (1 ml) and tetrahydrofuran (THF) (2.00 ml) were added and the mixture stirred at 80° C. for 1 hour. The solvent was removed in vacuo to give an orange solid which was triturated under ether and filtered. The solid was dissolved in water and then extracted with ether. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give the title compound as a yellow solid (9 mg).

1. waitthe reaction mixture was left
2. stirringto stir at 120° C. under nitrogen for 3 hours
3. customThe cooled reaction mixture
4. customThe column was flushed with methanol
5. washthe desired product was eluted with 2M ammonia in methanol
6. customThe solvent was removed in vacuo from the appropriate fractions
7. customto give a yellow solid
8. stirringthe mixture stirred at 80° C. for 1 hour
9. customThe solvent was removed in vacuo
10. customto give an orange solid which
11. customwas triturated under ether
12. filtrationfiltered
13. dissolutionThe solid was dissolved in water
14. extractionextracted with ether
15. customthe solvent was removed in vacuo

ORD-Eintrag

ord-fadb29b6ab57467a8de7e9646ec45e1c

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08329730B2