HCID 57815315, compound → HCID 57815387, compound

HRID 385579Notes

Reaction equation

[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([CH2:12][N:13]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:23][CH2:22]3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1>CO.[C].[Pd]>[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([CH2:12][N:13]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:32])[C:28]([F:30])([F:31])[F:29])[CH2:23][CH2:22]3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 47.5 °C

Procedure

To a solution of 0.30 g of tert-butyl ((7-oxo-7,8-dihydro-1,8-naphthyridin-2-yl)methyl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate in 40 mL of methanol, 0.10 g of 10% palladium-carbon was added, and the mixture was stirred at 45 to 50° C. for 9 hours 30 minutes under a hydrogen atmosphere. The reaction mixture was cooled to room temperature, the insoluble substance was filtered off, and the filtration residue was washed with methanol. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=100:3 to obtain 0.18 g of tert-butyl ((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)methyl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate as a colorless foam.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe insoluble substance was filtered off
washthe filtration residue was washed with methanol
distillationThe solvent was distilled off under reduced pressure
customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-21e6899c73ae448eaf10f0ae1dccd495
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367831B2

Reaction notes

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