Trifluoroacetic acid → Benzyl 3-methyl-2-oxo-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

HRID 1664803Notes

Reaction equation

HRID 1664803 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH:9]1[C:18]2([CH:23]=[CH:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11](COCC[Si](C)(C)C)[C:10]1=[O:42]>ClCCl>[CH3:8][CH:9]1[C:18]2([CH:19]=[CH:20][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:22][CH2:23]2)[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67440829Benzyl 3-methyl-2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Product 1

HCID 67440213Benzyl 3-methyl-2-oxo-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL, 53.8 mmol) was added to a solution of benzyl 3-methyl-2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2′,3,3′-tetrahydro-1H,1′H-spiro[1,8-naphthyridine-4,4′-pyridine]-1′-carboxylate (0.10 g, 0.20 mmol) in dichloromethane (2 mL). After 2 h, the reaction mixture was concentrated. The concentrated mixture was diluted in dichloromethane (2 mL) and ethane-1,2-diamine (4 mL) was added. After 1 h, the reaction mixture was concentrated and saturated aqueous sodium bicarbonate was added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. MS 364.1 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe concentrated mixture was diluted in dichloromethane (2 mL)
  3. additionethane-1,2-diamine (4 mL) was added
  4. waitAfter 1 h
  5. concentrationthe reaction mixture was concentrated
  6. additionsaturated aqueous sodium bicarbonate was added
  7. extractionThe mixture was extracted with dichloromethane (3×)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-359523175c494349a1337a2832601381
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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