HCID 86710379, compound → HCID 86710380, compound

HRID 1398393Notes

Reaction equation

HRID 1398393 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[C:8]1[CH:14]=[C:15]([O:20][CH2:21][C@@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:23][CH:24]([CH3:26])[CH3:25])[C:16]([CH:18]=[CH2:19])=[CH:17][C:7]2=1.[H][H]>CO.[Pd]>[CH2:18]([C:16]1[C:15]([O:20][CH2:21][C@@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:14][C:8]2[N:9]([CH3:13])[C:10](=[O:12])[C:11]3[C:6]([C:7]=2[CH:17]=1)=[CH:5][CH:4]=[N:3][C:2]=3[CH3:1])[CH3:19]

Participants

5

Reactant 2

HCID 86710379HCID 86710379, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86710380HCID 86710380, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-tert-butyl (1-((4,6-dimethyl-5-oxo-9-vinyl-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (50 mg, 0.107 mmol) in MeOH (3 mL) was degassed with nitrogen for 5 min, then palladium on carbon (1.143 mg, 10.74 μmol) was added. The reaction mixture was allowed to stir under a balloon of hydrogen for 16 h. The reaction mixture was then filtered through diatomaceous earth (Celite®) and the filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC (2% MeOH in MDC) to afford (S)-tert-butyl (1-((9-ethyl-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (31 mg, 0.058 mmol, 54% yield) as pale yellow solid. LC/MS, (ESI) m/z 468.5 [(M+H)+, calcd for C27H38N3O4 468.3]; LC/MS retention time (method D): tR=1.31 min.

Workup

  1. filtrationThe reaction mixture was then filtered through diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative TLC (2% MeOH in MDC)

Sources & evidence

ORD record
ord-a8382d2d92c24687b04f86d45ad17967
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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