Glyoxylic Acid → HCID 14557647, compound

To a stirred solution of 6-aminoquinoline (compound IV, FIG. 3B) (0.72 g, 5 mmol) in acetonitrile (20 ml) was added 33% aqueous glyoxylic acid (1.85 g, 20 mmole) solution. A solution of NaBH3CN (0.64 g, 10.2 mmol) in acetonitrile (20 ml) was then added at 3° C. over 20 minutes and the reaction mixture was warmed to room temperature and stirred for 48 hours. Acetonitrile was evaporated under vacuum, water (20 ml) was added to the residue, the solution was alkalinized to pH 9.5, and unreacted amine was extracted with ether. Concentrated HCl (25 ml) was added to the aqueous solution and the mixture was stirred at 25° C. for 1 hour. Solvent was evaporated under vacuum. The resultant residue of N-(6-quinolinyl)glycine was dissolved in dry ethanol (50 ml) saturated with dry HCl, stirred overnight and then refluxed for 3 hours. Ethanol was evaporated, the ester hydrochloride was suspended in dry ether, and ammonia gas was bubbled. The ammonium chloride was filtered and ether was removed by evaporation to give ethyl N-(6-quinolinyl)glycinate (0.5 g, 87%, mp 122-123° C.). N-(6-quinolinyl)glycine hydrazide (compound VI, FIG. 3B), synthesized by hydrazinolysis of the above ester, was reacted with 3,5-dibromo-2,4-dihydroxybenzaldehyde to give GlyH-126. Similar procedures were used for synthesis of GlyH-127.

1. customAcetonitrile was evaporated under vacuum, water (20 ml)
2. additionwas added to the residue
3. extractionwas extracted with ether
4. additionConcentrated HCl (25 ml) was added to the aqueous solution
5. stirringthe mixture was stirred at 25° C. for 1 hour
6. customSolvent was evaporated under vacuum
7. dissolutionThe resultant residue of N-(6-quinolinyl)glycine was dissolved in dry ethanol (50 ml) saturated with dry HCl
8. stirringstirred overnight
9. temperaturerefluxed for 3 hours
10. customEthanol was evaporated
11. customammonia gas was bubbled
12. filtrationThe ammonium chloride was filtered
13. customether was removed by evaporation

ORD record

ord-b5a11d892d5f4b53b1031240abce5f1e

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414037B2