1-Pyrrolidineethanamine → HCID 60682705, compound

To a stirred suspension of 2-hydroxyquinoline-4-carboxylic acid (preparation 10) (2.20 g, 12 mmol) in anhydrous DCM (60 ml), was added anhydrous DMF (36 drops) and thionyl chloride (3.3 ml, 46 mmol) under argon at room temperature. The mixture was refluxed for 3 h and then allowed to cool to room temperature. The solvents were removed under reduced pressure and the residue was dissolved in anhydrous THF (37 ml) under argon. 2-Pyrrolidin-1-ylethanamine (4.4 ml, 35 mmol) was added and the reaction was stirred at room temperature for 16 h. Solvents were removed under vacuum and the residue partitioned between NaHCO3 saturated aqueous solution (100 ml) and DCM (2×100 ml). The organic layers were combined, dried over MgSO4, filtrated and evaporated under reduced pressure. The crude was purified by column chromatography using a 24 g silica gel cartridge. Solvent A: DCM, Solvent B: 10% MeOH—NH3 in DCM. Gradient: 2 min hold 100% A followed by 18 min ramp to 40% B and then hold 5 min at 40% B. The desired fractions were combined and concentrated to dryness under reduced pressure to obtain the desired material as a white solid (2 g, 6.6 mmol, 56%).

1. temperatureThe mixture was refluxed for 3 h
2. customThe solvents were removed under reduced pressure
3. dissolutionthe residue was dissolved in anhydrous THF (37 ml) under argon
4. customSolvents were removed under vacuum
5. customthe residue partitioned between NaHCO3 saturated aqueous solution (100 ml) and DCM (2×100 ml)
6. dry with materialdried over MgSO4
7. filtrationfiltrated
8. customevaporated under reduced pressure
9. customThe crude was purified by column chromatography
10. custom2 min
11. waitfollowed by 18 min ramp to 40% B
12. waithold 5 min at 40% B
13. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-df073ed5011c47048403667c64d876a0

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115088B2