Acetic Acid → 5-(3-Methoxyphenyl)-3-(5-Methyl-1,2,4-oxadiazol-3-yl)-1,6-Naphthyridin-2(1H)-one

HRID 651232Notes

Reaction equation

HRID 651232 reaction equation
[C:1](O)(=O)[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[N:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[C:16]([C:24](=[N:26][OH:27])[NH2:25])[C:17](=[O:23])[NH:18]3)[CH:10]=[CH:11][CH:12]=1>CN(C=O)C>[CH3:1][C:2]1[O:27][N:26]=[C:24]([C:16]2[C:17](=[O:23])[NH:18][C:19]3[C:14]([CH:15]=2)=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[CH:8]=2)[N:22]=[CH:21][CH:20]=3)[N:25]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 136116127HCID 136116127, compound

Product 1

HCID 1354184045-(3-Methoxyphenyl)-3-(5-Methyl-1,2,4-oxadiazol-3-yl)-1,6-Naphthyridin-2(1H)-oneYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of acetic acid (0.90 g) in DMF (100 ml) was added N,N′-carbonyldiimidazole (2.43 g) and the mixture was stirred at 70° C. for 3 hours. To the solution was added 1,2-dihydro-5-(3-methoxyphenyl)-2-oxo-1,6-naphthyridin-3-amidoxime (3.10 g) prepared in the same manner as described in Example 1(1), and the mixture was stirred at 70° C. for 2 hours and further at 130° C. for 1 hour. The reaction mixture was concentrated to dryness under reduced pressure, and water was added to the residue, and the precipitated crystals were separated by filtration and washed with water, isopropanol and diisopropyl ether in this order and then dried. The resulting crystals were subjected to silica gel column chromatography and eluted with chloroform-methanol (50:1). The resulting crystals were recrystallized from chloroform-ethanol to give the title compound (2.22 g) as colorless crystals. M.p. 286-288° C. Hydrochloride of the title compound, M.p. 281-282° C. (recrystallized from ethanol).

Workup

  1. customprepared in the same manner
  2. stirringthe mixture was stirred at 70° C. for 2 hours and further at 130° C. for 1 hour
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure, and water
  4. additionwas added to the residue
  5. customthe precipitated crystals were separated by filtration
  6. washwashed with water, isopropanol and diisopropyl ether in this order
  7. customdried
  8. washeluted with chloroform-methanol (50:1)
  9. customThe resulting crystals were recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-0e190a9b0ca1452192c5c3e96119a318
Source dataset
uspto-grants-2001_08
Patent number
US06277993B1

Reaction notes

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