Diethyl Ether → HCID 21073853, compound

HRID 1373609Notes

Reaction equation

HRID 1373609 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20](=[O:24])[NH:21]2)=[C:16]([CH3:25])[CH:15]=1)C1C=CC=CC=1.CCOCC>CCO.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20](=[O:24])[NH:21]2)=[C:16]([CH3:25])[CH:15]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 21073832HCID 21073832, compound

Product 1

HCID 21073853HCID 21073853, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A sixth intermediate compound, 7-(4-Hydroxy-butoxy)-5-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one, was produced as follows: 7-(4-Benzyloxy-butoxy)-5-methyl-1H-[1,8]naphthyridin-2-one (7.31 g, 21.6 mmol) was hydrogenated using 20% Pd/C (1.0 g) in EtOH (100 mL). The product precipitated out of solution before the double bond was reduced. DMF (75 mL) was added and the mixture was heated to dissolve the solids. More 20% Pd/C (1.0 g) was added and the hydrogenation was continued, however the double bond was resistant to further hydrogenation under these conditions. The reaction mixture was filtered and the solvent was concentrated to give a slurry. Et2O was added and the solid was collected by filtration and dried to give 7-(4-hydroxy-butoxy)-5-methyl-1H-[1,8]naphthyridin-2-one (4.37 g, 17.6 mmol, 81%). 7-(4-Hydroxy-butoxy)-5-methyl-1H-[1,8]naphthyridin-2-one (3.0 g, 12.08 mmol) was hydrogenated using 20% Pd/C in acetic acid (mL) for x h. The reaction mixture was filtered and concentrated to give a mixture of the sixth intermediate compound and the corresponding acetylated compound. The mixture was suspended in MeOH (30 mL) and H2O (10 mL) and the pH was adjusted to 14 by addition of 50% aqueous NaOH. The mixture was warmed to 45° C. Glacial acetic acid was added to bring the pH to 7.5 and the MeOH was removed under reduced pressure. The resulting solid was filtered, washed with H2O and dried to give the sixth intermediate compound as a solid (2.78 g, 11.1 mmol, 92%). MS: APCI: M+1: 251.1 (Exact Mass: 250.13).

Workup

  1. customThe product precipitated out of solution before the double bond
  2. additionDMF (75 mL) was added
  3. temperaturethe mixture was heated
  4. dissolutionto dissolve the solids
  5. additionMore 20% Pd/C (1.0 g) was added
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe solvent was concentrated
  8. customto give a slurry
  9. filtrationthe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-5f730fc36aba41128c454bb3f8e75189
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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