Trifluoroacetic acid → 1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid [2-(2,2,2-trifluoro-acetylamino)-ethyl]amide

{2-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester (25 mg, 0.049 mmol) was dissolved in CH2Cl2 (2 mL). Trifluoroacetic acid (1 mL) was added, and the mixture was stirred for 2 h. Solvent and excess TFA was removed by evaporation, and to the residue were added THF (3 mL), triethylamine (0.034 mL, 0.24 mmol), and ethyl trifluoroacetate (2 mL). The resulting mixture was refluxed overnight, then concentrated to dryness. The residue was dissolved in EtOAc and washed with 0.1 M HCl. The organic layer was dried over MgSO4 and concentrated, and the crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 12.7 mg of the title compound as a light yellow solid. MS: (+) m/z 511.33 (M+1).

1. customSolvent and excess TFA was removed by evaporation
2. temperatureThe resulting mixture was refluxed overnight
3. concentrationconcentrated to dryness
4. dissolutionThe residue was dissolved in EtOAc
5. washwashed with 0.1 M HCl
6. dry with materialThe organic layer was dried over MgSO4
7. concentrationconcentrated
8. customthe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

ORD record

ord-51d7f581d35c482a97cf0c83e277ed8f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921389B2